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Synthesis process of levetiracetam

A technology of synthesis process and synthesis route, applied in the direction of organic chemistry, etc., can solve the problems of high cost input of hidden safety hazards and high optical isomers, and achieve the effect of low cost of safety input, high quality of finished products, and high environmental friendliness.

Active Publication Date: 2018-12-21
HONGGUAN BIO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, during the conversion from carboxylic acid to amide, highly toxic control products such as alkyl chloroformate are used
In commercial mass production, there are great potential safety hazards and cost investment in safety
Simultaneously, the levetiracetam finished product obtained by this process has higher optical isomers

Method used

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  • Synthesis process of levetiracetam
  • Synthesis process of levetiracetam
  • Synthesis process of levetiracetam

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The first step: the synthesis of (S)-2-(4-chlorobutanamide) butanamide

[0033] In a 2L reaction flask, add 1000mL of acetonitrile, add (S)-2-(4-chlorobutanamide)butyric acid (100.0g, 481.6mmol) under stirring, stir to dissolve, add (Boc) 2 O (126.1g, 577.8mmol), control the temperature in the reaction system to 20-30°C, slowly add pyridine (26.7g, 337.6mmol) dropwise to the reaction system for 20 minutes, and stir for 30 minutes after the addition is complete; Add ammonium bicarbonate (45.7 g, 578.1 mmol), and stir at 20 to 30°C for 5 to 8 hours; TLC spotting detects that the reaction of the raw materials is complete (developing solvent: ethyl acetate: glacial acetic acid = 100:1), and filter Remove the insoluble matter in the system, and concentrate the filtrate to dryness under reduced pressure; add the concentrate to acetone, heat to 60-70°C to dissolve until all dissolved, cool to 10-20°C, stir and crystallize for 2-3 hours; filter, reduce Drying under pressure ga...

Embodiment 2

[0037] The first step: the synthesis of (S)-2-(4-chlorobutanamide) butanamide

[0038] In a 2L reaction flask, add 1000mL of acetonitrile, add (S)-2-(4-chlorobutanamide)butyric acid (100.0g, 481.6mmol) under stirring, stir to dissolve, add (Boc) 2 O (126.1g, 577.8mmol), control the temperature in the reaction system to 20-30°C, slowly add pyridine (26.7g, 337.6mmol) dropwise to the reaction system for 20 minutes, and stir for 30 minutes after the addition is complete; Add ammonium carbonate (37.0g, 385.3mmol), stir and react at 20-30°C for 5-8 hours; TLC spot plate detection of raw material reaction is complete (developing solvent: ethyl acetate: glacial acetic acid = 100:1), filter to remove For the insoluble matter in the system, the filtrate is concentrated to dryness under reduced pressure; the concentrate is added to acetone, heated to 60-70°C to dissolve until completely dissolved, cooled to 10-20°C, stirred and crystallized for 2-3 hours; filtered, reduced pressure Aft...

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Abstract

The invention relates to the technical field of pharmaceutical preparation, in particular to a preparation method of an antiepileptic drug. The synthesis process of levetiracetam designed by the invention takes (S)-2-(4-chlorobutyramide) butyric acid as an initial raw material, pyridine as an alkali and (Boc)2O as an activating reagent of carboxylic acid, an ammonium salt is added to prepare (S)-2-(4-chlorobutyramide) butyramide, and finally a cyclization reaction is carried out in the presence of alkali to obtain levetiracetam. The process does not need chemical resolution, does not use highly toxic or corrosive chemical reagents, is simple to operate, mild in conditions, environment-friendly and high in finished product quality, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of medicine preparation, in particular to a preparation method of an antiepileptic drug. Background technique [0002] Epilepsy is a chronic syndrome of transient brain dysfunction, a common disease caused by neuronal synapse lesions. It is understood that there are tens of millions of epilepsy patients worldwide, a few of them can be completely treated, and most of them need to insist on long-term use of antiepileptic drugs to reduce seizures and create a good quality of life for patients. After a century of development, from the initial use of potassium bromide to the appearance of phenobarbital, and then to the advent of phenytoin and valproic acid in the last century, great progress has been made in the field of epilepsy treatment. Levetiracetam is a pyrrolidone antiepileptic drug, which can effectively control epileptic seizures. It has the characteristics of high therapeutic index, good safety, and mi...

Claims

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Application Information

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IPC IPC(8): C07D207/27
CPCC07D207/27
Inventor 于学彬卢天翼朱金龙吴杰张超
Owner HONGGUAN BIO PHARMA CO LTD
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