Method for synthesizing high-purity levetiracetam

A high-purity, ethyl-based technology, applied in the direction of organic chemistry, can solve the problems of high cost, low yield, harsh reaction conditions, etc., and achieve the effects of low cost, high yield and mild reaction conditions

Inactive Publication Date: 2010-11-17
SHANGHAI ECUST BIOMEDICINE CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has low yield, high cost, and harsh reaction conditions require low temperature (-30~-40°C)

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] 51.3 g of (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid and 120 mL of dichloromethane were put into a three-necked flask. Cool down to -10°C, add 47.8g of diisopropylethylamine and 35.7g of ethyl chloroformate in sequence, control the temperature at -5°C, and continue the reaction for 30 minutes. Keep the temperature at about -5°C, and react with ammonia gas until the conversion of raw materials is complete. After the reaction was completed, filter and wash the filter cake with dichloromethane. After the filtrate and washing liquid were combined, the residue obtained was concentrated under reduced pressure, recrystallized with 45 mL of ethyl acetate (containing 0.5% diisopropylethylamine), filtered with suction, and dried to obtain (S)-α-ethyl - 43 g of 2-oxo-1-pyrrolidineacetamide, yield 85%. The optical purity is 99.5%, the HPLC purity is 99.6%, and the impurity (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid content is 0.06%.

Embodiment 2

[0016] Add 55 g of (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid and 130 ml of dichloromethane into a three-necked flask. Add 51.2 g of diisopropylethylamine and 38.3 g of ethyl chloroformate in sequence, control the temperature at 25° C., and continue the reaction for 30 minutes. Keep the temperature at about 25°C, and react with ammonia gas until the raw materials are completely reacted. After the reaction was completed, filter and wash the filter cake with dichloromethane. The filtrate and washings were combined and concentrated under reduced pressure. The obtained residue was recrystallized by adding 50 mL of ethyl acetate (containing 0.5% triethylamine), suction filtered and dried to obtain (S)-α-ethyl-2-oxo-1-pyrrolidineacetamide 44.7 g. Yield 83%. The optical purity is 99.6%, the HPLC purity is 99.7%, and the impurity (S)-α-ethyl-2-oxo-1-pyrrolidineacetic acid content is 0.07%.

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Abstract

The invention relates to a method for synthesizing high-purity levetiracetam, belongs to the field of chemical synthesis and particularly relates to a method for preparing high-purity levetiracetam by substituting diisopropylethylamine for triethylamine in a reaction for preparing (S)-a-ethyl-2-oxo-1-pyrrolidineacetamide (levetiracetam) by ammoniation of (S)-a-ethyl-2-oxo-1-pyrrolidineacetic acid.

Description

technical field [0001] The invention relates to a preparation method of levetiracetam, which belongs to the field of chemical synthesis, in particular to the preparation of (S)-α by the ammoniation of (S)-α-ethyl-2-oxo-1-pyrrolidine acetic acid - In the reaction of ethyl-2-oxo-1-pyrrolidineacetamide (levetiracetam), triethylamine is replaced with diisopropylethylamine, and a method for preparing high-purity levetiracetam. Background technique [0002] Antiepileptic drugs are a class of drugs used to prevent and treat paroxysmal and temporary brain dysfunction caused by epileptic seizures. Levetiracetam (Levetiracetam) is developed by Belgian UCB company for the treatment of localized and secondary generalized epilepsy drugs. It is a second-generation acetylcholine agonist, a derivative of pyrrolidone, which has the unique pharmacological effects of limited selective protection and primary systemic epilepsy, and does not affect the metabolism of other antiepileptic drugs in ...

Claims

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Application Information

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IPC IPC(8): C07D207/27
Inventor 吴范宏张雷肖繁花王其蕊
Owner SHANGHAI ECUST BIOMEDICINE CO LTD
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