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Oxiracetam synthesis technology

A synthesis process and technology of the process route, applied in the field of medicine and chemical industry, can solve the problems of adding protection and deprotection steps, expensive amino protecting agents, difficult starting materials, etc., and achieves low cost, good industrial value, and simple operation. Effect

Inactive Publication Date: 2016-08-03
WUHAN INSTITUTE OF TECHNOLOGY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the one hand, the starting materials in this route are not easy to obtain, and the amino protecting agent used is expensive, and the production cost is higher; on the other hand, the increased protection and deprotection steps of this route reduce the yield

Method used

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Examples

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Effect test

Embodiment 1

[0030] A kind of preparation of 4-hydroxyl-2-oxo-1-pyrrolidine acetamide

[0031] 1) Preparation of ethyl 4-bromoacetoacetate: Control the temperature at -5~5°C, mix 26.03g of ethyl acetoacetate and 15mL of dichloromethane evenly, add 35.16g of bromine drop by drop, keep the reaction for 2h, pass into Dry nitrogen for 1 h, concentrate under reduced pressure to constant weight, and collect fractions at 85°C by oil pump vacuum distillation to obtain 38.69 g of transparent oily liquid ethyl 4-bromoacetoacetate, with a yield of 92.54%;

[0032] 2) Preparation of glycine methyl ester hydrochloride: Control the temperature at -5-5°C, add 23.56g of acetyl chloride dropwise to 60ml of anhydrous methanol, keep it warm for 1 hour after the drop, add 7.51g of glycine in 2 batches, After the addition, the system was heated to 70°C for 5 hours, concentrated under reduced pressure to remove excess solvent, and the residue was added with 30 ml of acetone and stirred for 5 hours, filtered, an...

Embodiment 2

[0036] A kind of preparation of 4-hydroxyl-2-oxo-1-pyrrolidine acetamide

[0037] 1) Preparation of ethyl 4-bromoacetoacetate: Control the temperature at -5~5°C, mix 30.03g of ethyl acetoacetate and 15mL of dichloromethane evenly, add 44.24g of bromine drop by drop, keep the reaction for 2h, pass into Dry nitrogen for 1 h, concentrate under reduced pressure to constant weight, and collect fractions at 85°C by oil pump vacuum distillation to obtain 38.69 g of transparent oily liquid ethyl 4-bromoacetoacetate, with a yield of 92.66%.

[0038] 2) Preparation of glycine ethyl ester: Control the temperature at -5~5°C, add 23.56g of acetyl chloride dropwise to 70ml of absolute ethanol, keep the reaction for 1h after dropping, add 7.51g of glycine in 2 batches, and complete the system Raise the temperature to 70°C for 5 hours, concentrate under reduced pressure to remove excess solvent, add 40ml of acetone to the residue and stir for 5h, filter, and vacuum-dry the filter cake to obta...

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Abstract

The invention belongs to the field of pharmaceutical chemicals and particularly relates to an oxiracetam synthesis technology, ethyl acetoacetate and glycine are taken as the raw materials, the ethyl acetoacetate is changed into 4-halogeneated ethyl acetoacetate by halogenation reaction, the 4-halogeneated ethyl acetoacetate and glycine ester formed by the glycine are cyclized to form 2,4-dioxo-1-pyrrolidine acetate, and 4-hydroxy-2-oxo-1-pyrrolidineacetamide is obtained after hydrolysis and aminolysis. According to the oxiracetam synthesis technology, the related raw materials are easy to obtain, and the synthesis technology is simple and has good industrial values.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and in particular relates to a synthesis process of oxiracetam. Background technique [0002] Oxiracetam, whose chemical name is 4-hydroxy-2-oxo-1-pyrrolidineacetamide, is a cyclic derivative of hydroxyaminobutyric acid (GABOB), which is a new generation of brain metabolism improving drugs, which can promote Phosphorylcholine and phosphorylethanolamine are synthesized to promote brain metabolism, stimulate the specific central nervous system through the blood-brain barrier, improve intelligence and memory, and are mainly used in the treatment of amnesia, senile dementia, and vascular dementia in clinical practice Wait. Its structural formula is as follows: [0003] [0004] Among the currently reported synthetic routes of oxiracetam, patent CN1513836A uses 4-halogenated acetoacetic acid derivatives as starting materials, undergoes condensation reaction with alkali metal or alkal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/273
CPCC07D207/273
Inventor 王凯孙新宇周霁苏云霞侯敏杨芳吴风收杨柯
Owner WUHAN INSTITUTE OF TECHNOLOGY
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