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Synthesis method of (S)-2-aminobutanamide

A technology of aminobutyramide and a synthesis method, applied in the field of pharmaceutical synthesis, can solve the problems of low atom utilization rate, high environmental hazard, long process route, etc., and achieves high HPLC purity and optical purity, small amount of three wastes, and easy availability of raw materials. Effect

Pending Publication Date: 2021-12-21
ZHEJIANG HUAHAI PHARMACEUTICAL CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The above synthetic routes all adopt the traditional chemical resolution method to construct the chiral center, the process route is long, and the utilization rate of atoms is low
At the same time, the solvents and reagents used in the chemical separation method are very harmful to the environment, and the amount of three wastes is large, which restricts industrial application to a certain extent.

Method used

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  • Synthesis method of (S)-2-aminobutanamide
  • Synthesis method of (S)-2-aminobutanamide
  • Synthesis method of (S)-2-aminobutanamide

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Enzymolysis reaction: add (R / S)-methyl 2-aminobutyrate (117g, 1mol) and H to the reaction flask 2 O (180g), heat up to 30°C under stirring, add immobilized bacterial agent (i.e. immobilized methylocystosis, preservation number is CCTCC NO: M2016494) (10g), control the temperature in the range of 25-35°C Inside, add dropwise 20% Na 2 CO 3 solution, keep the pH of the reaction system at 6.5 to 8.0, react until the isomer (R)-2-aminobutyric acid methyl ester is less than 1%, stop the reaction, filter, reclaim the immobilized bacterial agent, add the extractant toluene ( 200g), stirred for 30 minutes, stood for 30 minutes, separated layers, collected the organic phase, repeated the extraction operation 3 times, combined the organic phase, added anhydrous magnesium sulfate (20g) to the organic phase, stirred and dried for 30 minutes, filtered, collected Filtrate, carry out vacuum distillation to filtrate, control vacuum distillation temperature 50~60 ℃, vacuum distillation...

Embodiment 2

[0037] Enzymolysis reaction: add (R / S)-methyl 2-aminobutyrate (117g, 1mol) and H to the reaction flask 2O (120g), heat up to 30°C under stirring, add immobilized bacterial agent (i.e. immobilized methylocystosis, preservation number is CCTCC NO: M2016494) (6g), control the temperature in the range of 25-35°C Inside, add 20% K dropwise 2 CO 3 solution, keep the pH of the reaction system at 6.5 to 7.5, react until the isomer (R)-2-aminobutyric acid methyl ester is less than 1%, stop the reaction, filter, reclaim the immobilized bacterial agent, add the extractant toluene ( 150g), stirred for 30 minutes, stood still for 30 minutes, separated layers, collected the organic phase, repeated the extraction operation 3 times, combined the organic phase, added anhydrous sodium sulfate (20g) to the organic phase, stirred and dried for 30 minutes, filtered, collected Filtrate, the filtrate was subjected to vacuum distillation, controlled vacuum distillation temperature 50 ~ 60 ° C, vacu...

Embodiment 3

[0040] Enzymolysis reaction: add (R / S)-methyl 2-aminobutyrate (117g, 1mol) and H to the reaction flask 2 O (150g), heat up to 30°C under stirring, add immobilized bacterial agent (i.e. immobilized methylocystosis, preservation number is CCTCC NO: M2016494) (12g), control the temperature in the range of 25-35°C Inside, add dropwise 10% Na 2 CO 3 Solution, keeping the pH of the reaction system at 7.0 to 8.0, reacting to stop the reaction when the isomer (R)-2-aminobutyric acid methyl ester is less than 1%, filtering, reclaiming the immobilized bacterial agent, adding the extractant toluene ( 200g), stirring for 30 minutes, standing for 30 minutes, layering, collecting the organic phase, repeating the extraction operation 3 times, merging the organic phase, adding anhydrous sodium sulfate (20g) to the organic phase, stirring and drying for 30 minutes, filtering, collecting Filtrate, the filtrate was subjected to vacuum distillation, controlled vacuum distillation temperature 50...

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Abstract

The invention provides a method for preparing (S)-2-aminobutyric acid ester by an enzyme method, which comprises the following steps of: splitting (R / S)-2-aminobutyric acid ester serving as a raw material under the action of ester hydrolase to obtain (S)-2-aminobutyric acid ester, and further performing ammonolysis to obtain (S)-2-aminobutanamide. The method provided by the invention is simple to operate, the amount of three wastes is small, and the (S)-2-aminobutanamide obtained by the reaction is high in purity and completely meets the requirements of industrial production.

Description

(1) Technical field [0001] The invention relates to a synthesis method of an antiepileptic drug levetiracetam intermediate, belonging to the technical field of drug synthesis. (2) Background technology [0002] Levetiracetam is a broad-spectrum antiepileptic drug with high efficiency and low toxicity developed by UCB Company in Belgium. It is mainly used for the treatment of localized and secondary generalized epilepsy. Its chemical name is (S)-α-B Base-2-oxo-1-pyrrolidineacetamide. [0003] At present, there are many reports on the preparation methods of levetiracetam at home and abroad, mainly by chemical resolution synthesis. There are two types of synthetic methods commonly used in industry: [0004] (1) Developed by Belgian UCB Company, racemized (R / S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid is used as raw material, and (R)-α-methylbenzylamine is used as resolving agent , Split in benzene, and then treated with alkali to obtain (S)-α-ethyl-2-oxo-1-pyrrolidineacetic ac...

Claims

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Application Information

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IPC IPC(8): C07C237/06C07C231/02C12P13/00C12P41/00
CPCC07C231/02C12P41/005C12P13/001C07B2200/07C07C237/06C12P13/00C12P41/00C07C227/34
Inventor 郑晨光李敏勇龚玉龙朱元勋颜峰峰
Owner ZHEJIANG HUAHAI PHARMACEUTICAL CO LTD
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