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Preparation method of (s)-4-hydroxy-2-oxo-1-pyrrolidineacetamide

A technology of pyrrolidine acetamide and oxo, which is applied in directions such as organic chemistry, can solve the problems of high impurity content of levo-oxiracetam, unfavorable feeding method for industrialized production and the like, and achieves the effects of high purity, easy operation and quality improvement.

Active Publication Date: 2011-11-23
CHONGQING RUNZE PHARM CO LTD
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Problems solved by technology

[0005] But in practice, the feeding method of the above-mentioned preparation method is not conducive to industrial production, and the impurity content of the obtained levoxiracetam is also relatively high. We also found that there are different types of levoxiracetam in our work. Crystalline form of Levoxiracetam

Method used

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  • Preparation method of (s)-4-hydroxy-2-oxo-1-pyrrolidineacetamide

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Effect test

Embodiment 1

[0030] The preparation steps of levo-oxiracetam of the present invention are as follows:

[0031] 1. Put 65.0g of glycinamide hydrochloride, 500ml of absolute ethanol and 49.3g of sodium bicarbonate into a three-necked reaction flask, and raise the temperature to reflux under stirring;

[0032] 2. After heating to reflux for 2 hours, add 49.3g of sodium bicarbonate, then dropwise add (S)-4-chloro-3-hydroxybutyric acid ethyl ester 97.7g, continue the reflux reaction for 24h after the dropwise addition, and the reaction solution is slightly cooled After filtering, the filtrate was concentrated to obtain a reddish-brown oil;

[0033] 3. Dissolve the sample with 65ml of water, extract 260ml of dichloromethane four times (65ml each time), concentrate the aqueous solution to remove residual dichloromethane, pass through the 001X7 cation exchange resin after dilution of the aqueous solution, and collect the product containing part Neutralize with anion exchange resin 201X7, remove t...

Embodiment 2

[0037] The preparation steps of levo-oxiracetam are as follows:

[0038] 1. Put 65.0g of glycinamide hydrochloride, 500ml of absolute ethanol and 49.3g of sodium bicarbonate into a three-necked reaction flask, and raise the temperature to reflux under stirring;

[0039]2. After heating to reflux for 2 hours, add 49.3g of sodium bicarbonate, then dropwise add (S)-4-chloro-3-hydroxybutyric acid ethyl ester 97.7g, continue the reflux reaction for 24h after the dropwise addition, and the reaction solution is slightly cooled After filtering, the filtrate was concentrated to obtain a reddish-brown oil;

[0040] 3. Dissolve the sample with 65ml of water, extract with 260ml of dichloromethane, concentrate the aqueous solution to remove residual dichloromethane, pass the aqueous solution through 001X7 cation exchange resin after dilution, and neutralize the product-containing part of the collected liquid with anion exchange resin 201X7, and filter to remove Resin, the solution is conc...

Embodiment 3-6

[0043] Embodiment 3-6: Carry out according to following substance and its amount and process parameter, other are all identical with embodiment 1. The prepared levo-oxiracetam has a purity greater than 99.3%, and the impurity is 0-5%, calculated by mass percentage.

[0044] Reality

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Abstract

A preparation method of (s)-4-hydroxy-2-oxo-1-pyrrolidineacetamide. The preparation method comprises the following steps of crude product preparation and crystallization, wherein the step of crystallization adopts acetone and water as solvents. Levo-oxiracetam prepared through the preparation method has high purity above 99.3 wt% and low impurity content of 0 to 0.5 wt%. The preparation method has the advantages that a material addition mode adopted by the preparation method realizes that frequency of addition of an inorganic base is reduced; operation is simple; and the preparation method is in favor of industrialized production.

Description

technical field [0001] The invention relates to a preparation method of (S)-4-hydroxyl-2-oxo-1-pyrrolidineacetamide. Background technique [0002] (S)-4-Hydroxy-2-oxo-1-pyrrolidineacetamide is the levorotatory form of oxiracetam, and its commercial name is levo-oxiracetam (hereinafter referred to as levo-oxiracetam). Its chemical structure is as follows: [0003] [0004] The report on oxiracetam discloses that it is a synthetic hydroxyaminobutyric acid (GABOB) cyclic derivative, which can promote ATP in the brain, promote the synthesis of acetylcholine and enhance the conduction of nerve excitation, and it can prevent retrograde neuropathy caused by hypoxia. Sexual amnesia has improvement effect, can enhance memory, improve learning ability, is one of effective drugs for treating diseases such as Alzheimer's dementia (AD), cerebrovascular dementia (VD). In our research, we found that the above-mentioned efficacy of levo-oxiracetam is significantly better than that of o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/273
CPCC07D207/273
Inventor 陈宇瑛荣祖元李坤王瑛瑛罗刚薛雨邹云陈媛叶雷金磊冯华李飞王志强游潮
Owner CHONGQING RUNZE PHARM CO LTD
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