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Purification method for sinistrogyration oxiracetam

A purification method, the technology of ice water, applied in the direction of organic chemistry, etc., can solve the problems of complex purification process of levoxiracetam and low product purity, and achieve the effect of low production cost, high purity and simple method

Inactive Publication Date: 2012-07-04
CHONGQING RUNZE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But at present, the purification process of levo-oxiracetam is complicated or the purity of the obtained product is not high, it is difficult to obtain high-purity levo-oxiracetam under the conditions of low cost and simple process

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] A method for purifying levoxiracetam, as follows:

[0025] Add 0.75 ml of water to dissolve 1 g of levo-oxiracetam crude product (purity 89%), add propanol organic solvent dropwise until the solution is just turbid, and place it at 9°C for 30 hours, and a colorless transparent crystal precipitates, filter, add 2°C, Top-wash with 2 ml of ice water, and vacuum-dry at 28°C for 4.5 hours to obtain 0.5 g of colorless crystals with a purity of 98.2% by HPLC.

[0026] The preparation method of above-mentioned levo-oxiracetam crude product, its concrete steps are:

[0027] (a) Put 28.50 g of glycinamide hydrochloride, 20.65 g of sodium bicarbonate and 200 ml of absolute ethanol into a three-necked reaction flask, control the pH value to about 7.4, and heat up to reflux under stirring;

[0028] (b) After 2 hours of reflux, 39.08 g of (S)-4-chloro-3-hydroxybutyric acid ethyl ester was gradually added dropwise. During the dropwise addition, 20.65 g of the remaining sodium bicarbo...

Embodiment 2

[0032] A method for purifying levoxiracetam, as follows:

[0033] Add 5kg of levo-oxiracetam crude product (89% purity) to dissolve in 6 liters of water, add ethanol, propanol or isopropanol organic solvent dropwise until the solution is just turbid, place it at 12°C for 29 hours, and precipitate colorless transparent crystals, filter , Add 5°C, 4 liters of ice water for top washing, and vacuum-dry at room temperature for 5 hours to obtain 2.5 kg of colorless crystals with a purity of 98% by HPLC.

Embodiment 3

[0035] A method for purifying levoxiracetam, as follows:

[0036] Add 1.5 liters of water to dissolve 1 kg of levo-oxiracetam crude product (purity 89%), add THF organic solvent dropwise until the solution is just turbid, leave it at 6°C for 30 hours, and precipitate colorless transparent crystals, filter, add 0.5 liters at 1°C Top wash with ice water at 2°C, and vacuum-dry at 28°C for 4 hours to obtain 0.4 kg of colorless crystals with a purity of 97.8% by HPLC.

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Abstract

Provided is a purification method for sinistrogyration oxiracetam. The method comprises the steps of adding sinistrogyration oxiracetam coarse products in water for dissolving, dropping organic solvent in solution to enable the solution to become turbid just, standing at 0-18 DEG C for 1-3 days, separating out colorless transparent crystals, filtering, washing by using ice water at the temperature of 0-5 DEG C in a top mode, and drying in a vacuumizing mode to obtain the sinistrogyration oxiracetam with high purity. By means of the corresponding purification process using water as the organic solvent in the purification method, 89% of purity of the sinistrogyration oxiracetam coarse products is effectively increased to 97.5-98.2% of high performance liquid chromatography (HPLC) purity, and the purity of the sinistrogyration oxiracetam is greatly improved. Simultaneously, the purification method is simple, mild in control conduction, low in cost of production and applicable to large-scale industrial production.

Description

technical field [0001] The invention relates to a crystallization purification method, in particular to a crystallization purification method of (S)-4-hydroxy-2-oxo-1-pyrrolidineacetamide. Background technique [0002] Olaxiracetam is a nootropic drug synthesized for the first time in 1974 by the Italian Skelebechem Company, and the drug was launched in Italy in 1987. (S)-oxiracetam is a single enantiomer of oxiracetam, the chemical name is (S)-4-hydroxy-2-oxo-1-pyrrolidineacetamide (hereinafter referred to as levo-oxiracetam) , its chemical structure is as follows: [0003] [0004] Oxiracetam can promote the synthesis of phosphorylcholine and phosphorylethanolamine, promote brain metabolism, stimulate the specific central nervous system through the blood-brain barrier, increase the ratio of ATP / ADP in the brain, and make the protein and nucleic acid in the brain more stable. Increased synthesis can improve the memory and learning functions of patients with mental reta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/273
CPCC07D207/273
Inventor 叶雷荣祖元
Owner CHONGQING RUNZE PHARM CO LTD
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