CN108409589A - A kind of preparation method of the beta-amino acid esters of band chirality - Google Patents
A kind of preparation method of the beta-amino acid esters of band chirality Download PDFInfo
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- CN108409589A CN108409589A CN201810252541.1A CN201810252541A CN108409589A CN 108409589 A CN108409589 A CN 108409589A CN 201810252541 A CN201810252541 A CN 201810252541A CN 108409589 A CN108409589 A CN 108409589A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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- C07B2200/07—Optical isomers
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Abstract
The invention discloses a kind of preparation method of the beta amino acids ester of band chirality, step is：First beta amino acids raceme is prepared by being reacted with malonic acid and ammonium acetate halobenzene formaldehyde, it is reacted again with thionyl chloride by beta amino acids raceme and prepares beta amino acids ester raceme, split beta amino acids ester raceme and prepare with chiral beta amino acids ester.Method synthesis step disclosed by the invention is short, the period is short, at low cost, total recovery is high, can be used for industrialized production.
Description
Technical field
The invention belongs to amino-acid esters to synthesize field, and in particular to a kind of preparation method of the beta-amino acid esters of band chirality.
Background technology
Amino acid is the basic unit of constitutive protein matter, and very important work is played in human body and animal life activity
With.Optics pure amino acid is the important intermediate of the drugs such as synthesis polypeptide and lactam antibiotics, in pharmaceutical synthesis, new material
Synthesis, the exploitation of food additives and fine chemicals etc. all have huge application value.However, artificial synthesized ammonia
Base acid is racemic modification mostly, and in most cases, two isomers of DL-Amino Acid have different physiological actions, have
When even pharmacological property completely on the contrary, to DL-Amino Acid carry out split be it is a kind of obtain chiral amino acid important method.Currently,
The method for splitting of alpha amino acid mainly has chemical resolution method, chiral film Split Method, Chromatographic resolution method, enzyme Split Method, induction crystallisation
With extraction Split Method etc..But the method for splitting of beta amino acids is but reported seldom.
1999, Younghee Lee et al. were in document " Traceless Solid-Phase Synthesis of
Chiral 3-Arylβ-Amino Acid Containing Peptides Using a Side-Chain-Tetheredβ-
Using p-bromobenzaldehyde as starting material in Amino Acid Building Block ", chiral β-has been obtained by three-step reaction
Amino-acid ester (formula 1), but the route has following shortcoming：First step chiral source is too expensive；Second step reaction temperature is -78
DEG C, consersion unit is required high.
2009, Vicente Gotor et al. were in document " Stereoselective Chemoenzymatic
Preparation of b-Amino Esters:Molecular Modelling Considerations in Lipase-
With racemization in Mediated Processes and Application to the Synthesis of (S)-Dapoxetine "
Beta-amino acid esters be starting material, use PCL as chiral resolving agent, the beta-amino acid esters and S- of R- configurations obtained by a step
The chiral amino acid (formula 2) of configuration, although this reaction is simple, PCL enzymes are expensive.
2010, Guohua Hou et al. were in document " Highly Efficient Iridium-Catalyzed
It is former for starting with compound 1 in Asymmetric Hydrogenation of Unprotected β-Enamine Esters "
Material, by the beta-amino acid esters (formula 3) of chiral ligand catalyst one-step synthesis chirality, the route reaction is simple, but used
Chiral ligand is expensive.
In conclusion the raw materials used price height of the method for the beta-amino acid esters of existing anamorphic zone hand-type, severe reaction conditions,
To equipment requirement height.
Invention content
It is an object of the invention to：In view of the above problems, the present invention provides a kind of beta-amino acids of band chirality
The preparation method of ester, this method use splitting step, are split to obtain with chirality to the beta-amino acid esters raceme of synthesis
Beta-amino acid esters.The method step is short, at low cost, technological operation is convenient, the total recovery of safety and the beta-amino acid esters with chirality
It is high.
The technical solution adopted by the present invention is as follows：A kind of preparation method of the beta-amino acid esters of band chirality, including three anti-
Answer step：
(1) preparation of beta-amino acids raceme：
(2) preparation of beta-amino acid esters raceme
(3) fractionation of beta-amino acid esters
Wherein, in three steps, one kind in X F, Cl, Br；The resolving agent is PA ase PGA, asparagus fern ammonia
At least one of acid, preferably asparatate.
The specific operation process of the step (3) is as follows：The beta-amino acid esters raceme prepared by step (2) is dissolved in
A small amount of deionized water is added in organic solvent, adds resolving agent, controls the temperature of reaction system in whole process at 26-30 DEG C,
Reaction continues 24-36h, is isolated and purified, and obtains with chiral beta-amino acid esters.
Further, the organic solvent be tetrahydrofuran, DMF, acetone, ether, DMSO, methanol, in acetonitrile at least
The mass ratio of one kind, the beta-amino acid esters raceme and organic solvent is 1：10.0-1:13.5, preferably 1:10.
Further, the equivalent proportion of beta-amino acid esters raceme and resolving agent is 1 in the step (3):0.3-1:0.8,
It is preferred that 1:0.7.
Specifically, it prepares with chiral beta-amino acid esters, needs beta-amino acid esters raceme being dissolved in suitable organic
In solvent, and resolving agent appropriate is added and is split, be allowed to react at a certain temperature the regular hour, then detach pure
Change is handled.In preparation process, the amount of organic solvent and resolving agent need to be controlled strictly, can just prepare the band chirality of high yield
Beta-amino acid esters.
The concrete operation step that isolates and purifies in the step (3) is：Filtered crude product is split by 2-4 recrystallization
After optical purity, that is, ee values are up to standard, filtering, solid adds water, and adjust pH with wet chemical carries out salt between 9-10
Solution, then carries out product extraction, then wash, filter, be concentrated to dryness through salt, solubilizer stirring and crystallizing, mistake at 0-5 DEG C with ethers
Filter, the beta-amino acid esters of drying band chirality.
Further, the extraction is at least one of methyl tertiary butyl ether(MTBE), ethyl tert-butyl ether (ETBE), ether with ether, excellent
Select methyl tertiary butyl ether(MTBE)；The crystallization is petroleum ether, normal heptane, ether, chloroform, carbon tetrachloride, benzene, dimethyl formyl with solvent
At least one of amine, dimethyl sulfoxide, preferably petroleum ether.
Specifically, the selection of extraction ether and crystallization solvent directly affects extraction and crystallization effect, and extracts and crystallization
Effect further influence the yield with chiral beta-amino acid esters.
In conclusion by adopting the above-described technical solution, the beneficial effects of the invention are as follows：The present invention is with to halobenzene formaldehyde
It for starting material, is obtained by the reaction with chiral beta-amino acid esters by 3 steps, the method applied in the present invention is of low cost, easy
Easy, not high to equipment requirement, safety and total recovery height are suitable for industrial applications.
Description of the drawings
Examples of the present invention will be described by way of reference to the accompanying drawings, wherein：
Fig. 1：Prepare the reaction equation with chiral beta-amino acid esters.
Specific implementation mode
All features disclosed in this specification or disclosed all methods or in the process the step of, in addition to mutually exclusive
Feature and/or step other than, can combine in any way.
According to the above of description of the invention (including any accessory claim, abstract), according to the general of this field
Logical technological know-how and customary means can also be made other a variety of under the premise of not departing from above-mentioned basic fundamental thought of the invention
Modification, replacement or the change of form.The techniques implemented on the basis of the foregoing are all within the scope of the present invention.
Embodiment 1
The method for splitting of beta-amino acid esters, is shown below：
By 3- amino -3- (4- bromophenyls) methyl propionate (1.6kg, 1.0eq), D-ASP (0.51kg,
0.7eq), deionized water (2.0kg) is sequentially added in tetrahydrofuran (16.0kg) solution, after being warming up to 26-30 DEG C, keeps the temperature 26-
24-36h is reacted at 30 DEG C, after Solid-state Optics purity, that is, ee values are controlled in sampling between 85-93%, remaining system all filters
To solid A1.Then solid A1 is added in tetrahydrofuran (10.0kg) solution, after keeping the temperature 26-30 DEG C of reaction 12-24h, is taken
After the ee values of control solid are between 95-98% in sample, solid A2 is all obtained by filtration in remaining system, and then solid A2 is added again
Into tetrahydrofuran (8.0kg) solution, after keeping the temperature 26-30 DEG C of reaction 12-24h, solid ee values are controlled in sampling between 98-99%
Afterwards, the very high solid A3 of chiral purity is all obtained by filtration in remaining system, and solid A3 is added in tap water (5.0kg), uses
Wet chemical tune pH=9-10 solves salt, and product is extracted with methyl tertiary butyl ether(MTBE) (8.0kg), and organic phase is carried out again after salt washes,
Filtering, concentration is dry, adds stirring and crystallizing at 0-10 DEG C of petroleum ether (2.0kg), filters, and drying is obtained with chiral beta-amino acid esters
(0.45kg), ee%=99.3%, yield：28%.
Embodiment 2
The method for splitting of beta-amino acid esters, is shown below：
By 3- amino -3- (4- bromophenyls) methyl propionate (1.6kg, 1.0eq), D-ASP (0.43kg,
0.6eq), deionized water (2.0kg) is sequentially added in tetrahydrofuran (16.0kg) solution, after being warming up to 26-30 DEG C, keeps the temperature 26-
After 30 DEG C of reaction 24-36h, after Solid-state Optics purity, that is, ee values are controlled in sampling between 85-93%, remaining system all filters
To solid A1.Then solid A1 is added in tetrahydrofuran (10.0kg) solution, after keeping the temperature 26-30 DEG C of reaction 12-24h, is taken
After solid ee values are controlled in sample between 95-98%, solid A2 is all obtained by filtration in remaining system, is then again added to solid A2
In tetrahydrofuran (8.0kg) solution, after keeping the temperature 26-30 DEG C of reaction 12-24h, solid ee values are controlled in sampling between 95-98%
Afterwards, the very high solid A3 of chiral purity is all obtained by filtration in remaining system, and solid A3 is added in tap water (5.0kg), uses
Wet chemical tune pH=9-10 solves salt, and product is extracted with methyl tertiary butyl ether(MTBE) (8.0kg), and organic phase is carried out again after salt washes,
Filtering, concentration is dry, adds stirring and crystallizing at 0-10 DEG C of petroleum ether (2.0kg), filters, and drying is obtained with chiral beta-amino acid esters
(0.48kg), ee%=97.0%, yield：30%.
Embodiment 3
The method for splitting of beta-amino acid esters, is shown below：
By 3- amino -3- (4- bromophenyls) methyl propionate (1.6kg, 1.0eq), D-ASP (0.36kg,
0.5eq), deionized water (2.0kg) is sequentially added in tetrahydrofuran (16.0kg) solution, after being warming up to 26-30 DEG C, keeps the temperature 26-
After 30 DEG C of reaction 24-36h, after Solid-state Optics purity, that is, ee values are controlled in sampling between 50-57%, remaining system all filters
To solid A1.Then solid A1 is added in tetrahydrofuran (10.0kg) solution, after keeping the temperature 26-30 DEG C of reaction 12-24h, is taken
After solid ee values are controlled in sample between 53-58%, solid A2 is all obtained by filtration in remaining system, is then again added to solid A2
In tetrahydrofuran (8.0kg) solution, after keeping the temperature 26-30 DEG C of reaction 12-24h, solid ee values are controlled in sampling between 55-62%
Afterwards, the solid A3 of chiral purity is all obtained by filtration in remaining system, and solid A3 is added in tap water (5.0kg), carbonic acid is used
Aqueous solutions of potassium tune PH=9-10 solves salt, and product is extracted with methyl tertiary butyl ether(MTBE) (8.0kg), and organic phase is carried out again after salt washes, filtering,
Concentration is dry, adds stirring and crystallizing at 0-10 DEG C of petroleum ether (2.0kg), filters, and drying is obtained with chiral beta-amino acid esters
(0.62kg), ee%=61%, yield：39%.
It is found by the comparison of embodiment 1,2,3, when the equivalent proportion of beta-amino acid esters raceme and resolving agent is 1:0.7
When, the optical purity of the beta-amino acid esters of obtained band chirality is relatively high, illustrates that the dosage of resolving agent occupies in this invention
Important function.Peak area ratio shown in embodiment 1,2,3 from table 1 to finding, tear open by the peak area difference maximum at peak 1 and peak 2
Divide effect best for 1 products therefrom of embodiment, the dosage that resolving agent also can be explained has apparent influence to splitting effect.
Embodiment 4
The method for splitting of beta-amino acid esters, is shown below：
By 3- amino -3- (4- bromophenyls) methyl propionate (1.6kg, 1.0eq), D-ASP (0.51kg,
0.7eq), deionized water (2.0kg) is sequentially added in tetrahydrofuran (16.0kg) solution, after being warming up to 26-30 DEG C, keeps the temperature 26-
24-36h is reacted at 30 DEG C, after Solid-state Optics purity, that is, ee values are controlled in sampling between 85-93%, remaining system all filters
To solid A1.Then solid A1 is added in tetrahydrofuran (10.0kg) solution, after keeping the temperature 26-30 DEG C of reaction 12-24h, is taken
After the ee values of control solid are between 95-98% in sample, solid A2 is all obtained by filtration in remaining system, and then solid A2 is added again
Into tetrahydrofuran (8.0kg) solution, after keeping the temperature 26-30 DEG C of reaction 12-24h, solid ee values are controlled in sampling between 98-99%
Afterwards, the very high solid A3 of chiral purity is all obtained by filtration in remaining system, and solid A3 is added in tap water (5.0kg), uses
Wet chemical tune PH=9-10 solves salt, and product is extracted with methyl tertiary butyl ether(MTBE) (8.0kg), and organic phase is carried out again after salt washes,
Filtering, concentration is dry, adds stirring and crystallizing at 0-10 DEG C of normal heptane (2.0kg), filters, and drying is obtained with chiral beta-amino acid esters
(0.40kg), ee%=89.1%, yield：24.8%.
Compared and found by embodiment Isosorbide-5-Nitrae, the type of crystallization solvent can influence the yield with chiral beta-amino acids ester and
Optical purity, when crystallization is petroleum ether with solvent, yield and optical purity with chiral beta-amino acids ester are higher.
Embodiment 5
The method for splitting of beta-amino acid esters, is shown below：
By 3- amino -3- (4- bromophenyls) methyl propionate (1.6kg, 1.0eq), D-ASP (0.43kg,
0.6eq), deionized water (2.0kg) is sequentially added in acetone (16.0kg) solution, after being warming up to 26-30 DEG C, keeps the temperature 26-30 DEG C
After Solid-state Optics purity, that is, ee values are controlled after reacting 24-36h, in sampling between 85-93%, remaining system is all obtained by filtration solid
Body A1.Then solid A1 is added in acetone (10.0kg) solution, after keeping the temperature 26-30 DEG C of reaction 12-24h, is controlled in sampling solid
After body ee values are between 95-98%, solid A2 is all obtained by filtration in remaining system, and solid A2 is then added to acetone again
In (8.0kg) solution, after keeping the temperature 26-30 DEG C of reaction 12-24h, after solid ee values are controlled in sampling between 95-98%, remaining body
All the very high solid A3 of chiral purity is obtained by filtration in system, and solid A3 is added in tap water (5.0kg), water-soluble with potassium carbonate
Liquid tune pH=9-10 solves salt, and product is extracted with methyl tertiary butyl ether(MTBE) (8.0kg), and organic phase carries out after salt washes, filtering, concentration again
It is dry, add stirring and crystallizing at 0-10 DEG C of petroleum ether (2.0kg), filters, drying is obtained with chiral beta-amino acid esters (0.40kg),
Ee%=95.0%, yield：25%.
[table 1]
It is found by the comparison of embodiment 2,5, when reaction dissolvent is tetrahydrofuran, gained is with chiral beta-amino acids ester
Optical purity declines, and yield also decreases, illustrates in this invention, and the selection of step (3) solvent can influence band chiral beta-ammonia
The yield and optical purity of base acid esters.
Table 1 shows the liquid chromatography results of 1,2,3,4 and 5 products therefrom of embodiment, as it can be seen from table 1 peak face
Product moment it is different it is maximum for 1 products therefrom of embodiment namely its split effect it is best；Pass through the comparison of embodiment 1,2,3, embodiment
The comparison of the comparison and embodiment 2,5 of Isosorbide-5-Nitrae, can be further appreciated that, the amount ratio of beta-amino acid esters raceme and resolving agent
Example, the selection of crystallization solvent and reaction dissolvent influence the optical purity with chiral beta-amino acids ester and yield.Institute of the present invention
It states embodiment and does not limit claims of the present invention, specification and Figure of description, abstract and Figure of abstract, in the present invention
The qualifications not occurred in embodiment not indicate that the present invention is not claimed, but the embodiment mistake applied according to the present invention
It is more, it is difficult exhaustion.
In conclusion the method for the fractionation disclosed by the invention for preparing beta-amino acid esters is all made of common agents, raw material at
This is low, and the fractionation time is short, and high income, the reaction condition of no harshness is safe, easy to operate and environmentally friendly, is suitable for advising greatly
Mould industrialized production.
The invention is not limited in specific implementation modes above-mentioned.The present invention, which expands to, any in the present specification to be disclosed
New feature or any new combination, and disclose any new method or process the step of or any new combination.
Claims (6)
1. a kind of preparation method of the beta-amino ester acid of band chirality, which is characterized in that including three reaction steps：
(1) preparation of beta-amino acids raceme：
(2) preparation of beta-amino acid esters raceme
(3) fractionation of beta-amino acid esters
Wherein, in three steps, one kind in X F, Cl, Br；The resolving agent is in PA ase PGA, aspartic acid
At least one, preferred asparatate.
2. a kind of preparation method of the beta-amino ester acid of band chirality according to claim 1, which is characterized in that the step
(3) specific operation process is as follows：The beta-amino acid esters raceme prepared by step (2) is dissolved in organic solvent, is added few
Deionized water is measured, resolving agent is added, the temperature of reaction system in whole process is controlled at 26-30 DEG C, reacts and continue 24-36h,
It is isolated and purified, is obtained with chiral beta-amino acid esters.
3. a kind of preparation method of the beta-amino acid esters of band chirality according to claim 2, which is characterized in that described organic
Solvent is at least one of tetrahydrofuran, DMF, acetone, ether, DMSO, methanol, acetonitrile, the beta-amino acid esters raceme
Mass ratio with organic solvent is 1：10-1:13.5, preferably 1:10.
4. a kind of preparation method of the beta-amino acid esters of band chirality according to claim 2, which is characterized in that the step
(3) equivalent proportion of beta-amino acid esters raceme and resolving agent is 1 in:0.3-1:0.8, preferably 1:0.7.
5. a kind of preparation method of the beta-amino acid esters of band chirality according to claim 2, which is characterized in that the step
(3) concrete operation step that isolates and purifies in is：Filtered crude product is split by 2-4 recrystallization until optical purity i.e. ee
Be worth it is up to standard after, filtering, solid adds water, and adjust pH with wet chemical carries out salt solution between 9-10, is then carried out with ethers
Product extracts, then is washed through salt, filter, be concentrated to dryness, solubilizer stirring and crystallizing at 0-5 DEG C, filtering, drying band chirality
Beta-amino acid esters.
6. a kind of preparation method of the beta-amino ester acid of band chirality according to claim 5, which is characterized in that the extraction
It is at least one of methyl tertiary butyl ether(MTBE), ethyl tert-butyl ether (ETBE), ether, preferably methyl tertiary butyl ether(MTBE) with ether；The crystallization is used
Solvent is petroleum ether, normal heptane, ether, chloroform, carbon tetrachloride, benzene, dimethylformamide, at least one of dimethyl sulfoxide,
It is preferred that petroleum ether.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107602317A (en) * | 2017-08-02 | 2018-01-19 | 凯莱英医药集团（天津）股份有限公司 | The preparation method of the chiral Arvlacetic derivatives of 2 amino 2 |
| CN111333552A (en) * | 2020-04-09 | 2020-06-26 | 广州安岩仁医药科技有限公司 | β -benzo amino acid compound synthesis method |
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Cited By (3)
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| CN107602317A (en) * | 2017-08-02 | 2018-01-19 | 凯莱英医药集团（天津）股份有限公司 | The preparation method of the chiral Arvlacetic derivatives of 2 amino 2 |
| CN111333552A (en) * | 2020-04-09 | 2020-06-26 | 广州安岩仁医药科技有限公司 | β -benzo amino acid compound synthesis method |
| CN111333552B (en) * | 2020-04-09 | 2021-07-20 | 广州安岩仁医药科技有限公司 | Synthesis method of beta-benzo amino acid compound |
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