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Method for preparing levetiracetam

A technology for methionine and products, applied in the direction of organic chemistry, etc., can solve the problems of reduced yield and suboptimal synthesis process, and achieves the effects of simple operation, easy availability of raw materials, and simple operation steps.

Inactive Publication Date: 2010-01-13
BENGBU BBCA MEDICINE SCI DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And because the synthesis process does not reach the optimum, the yield is further reduced

Method used

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  • Method for preparing levetiracetam
  • Method for preparing levetiracetam
  • Method for preparing levetiracetam

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The first step: the synthesis of (S)-ethylglycine

[0024] Dissolve L-methionine (50 g, 336 mmoL) in 4 L of distilled water, then add 500 g of T-1 Raney nickel, stir vigorously and heat. React at 75-80°C for 4h, cool down and filter to remove the catalyst. The filtrate was treated with 1% 8-hydroxyquinoline in CHCl 3 Liquid extraction (2×1000mL), then CHCl 3 Wash (3 x 1200 mL). The washed aqueous phase was concentrated and evaporated to obtain 32.0 g of the product, the purity of which was detected by normalization by gas chromatography was 98.9%, the yield was 95.0%, and the melting range was 273-275°C.

[0025] The second step: the synthesis of (S)-ethylglycine methyl ester hydrochloride

[0026] (S)-Ethylglycine (25.76g, 230mmol) was added to 150mL of anhydrous methanol, stirred, and 37.0mL of thionyl chloride was slowly added dropwise at -10°C, after the drop was completed, the temperature was naturally raised to room temperature and stirred for 5h , the solven...

Embodiment 2

[0033] Except that the first step is different from the first step of embodiment 1, others are the same, and the following embodiments are the same.

[0034] Operate in the same way as in the first step of Example 1, only change the T-1 Raney nickel 500g used therein to 300g of W-2 Raney nickel, and keep the others unchanged to obtain (S)-ethylglycine 31.5g, which is normalized by gas chromatography The purity detected by Yihua is 99.0%, the yield is 94.8%, and the melting range is 273-275°C.

[0035] Total yield based on L-methionine: 47.8%.

Embodiment 3

[0037] Operate in the same way as in the first step of Example 1, only change the T-1 Raney nickel 500g used therein to 320g of W-2 Raney nickel, and the others remain unchanged to obtain (S)-ethylglycine 32.0g, and the gas chromatography normalized The purity detected by Yihua is 99.0%, the yield is about 95.0%, and the melting range: 273-275°C.

[0038] The total yield in terms of L-methionine is about: 48.0%.

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Abstract

The invention discloses a method for preparing levetiracetam, which is characterized by using methionine as a raw material to prepare levetiracetam through the steps of desulfurization, methylation, esterification, ammonolysis, amidation and intramolecular condensation cyclic reaction. The technical steps of the method are suitable for technologized production, and the improved technology has no strict reaction conditions. The raw material is easy to obtain, the operation is simple, the yield is high, and methanol and other solvents in preparation process can be recycled without generating the three wastes.

Description

technical field [0001] The invention relates to a preparation method of levetiracetam. Background technique [0002] Epilepsy is a common disease in the population, and it is widely distributed in countries all over the world. Antiepileptic drugs are generally amide nootropics or choline agonists. At present, since the Belgian UCB company developed piracetam, it has successively developed antiepileptic drugs such as oxiracetam, aniracetam, pramiracetam, etiracetam, neriracetam and nefiracetam . In the mid-term, levetiracetam has obvious antiepileptic effect and little adverse reaction, and it is widely used as an antiepileptic drug. [0003] There are two synthetic routes of levetiracetam: one is to use pyrrolidone as the starting material, and prepare 2-pyrrolidone sodium salt by reacting with sodium methoxide, then react with methyl α-bromobutyrate, and then undergo hydrolysis and acidification to obtain racemate (±)-α-ethyl-(2-oxo-1-pyrrolidinyl)acetic acid, and then ...

Claims

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Application Information

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IPC IPC(8): C07D207/27
Inventor 陈文婕韦亚锋江立新赵辉
Owner BENGBU BBCA MEDICINE SCI DEV
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