Preparation method of chiral cyclopropyl amino acid

A cyclopropyl and amino acid technology, which is applied in the field of simple preparation of chiral cyclopropyl amino acids, can solve the problems of affecting the reaction yield, numerous reaction steps, cumbersome operation, etc. the effect of pressure
CN107445894AInactive Publication Date: 2017-12-08WUHAN UNIV OF TECH
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
WUHAN UNIV OF TECH
Publication Date
2017-12-08
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention discloses a preparation method of chiral cyclopropyl amino acid. The preparation method comprises the following steps: mixing N-(2-formyl-4-methyl phenyl)-4-toluenesulfonamide with ethyl-2-benzoyl-1-chlorocyclopropane carboxylic acid with cesium carbonate in an N,N-dimethylformamide solvent, wherein the molar ratio of N-(2-formyl-4-methyl phenyl)-4-toluenesulfonamide to ethyl-2-benzoyl-1-chlorocyclopropane carboxylic acid to cesium carbonate is 1: 1: 1, the reaction temperature is room temperature and the reaction time is 1-2h; and after reaction, adding water and dichloromethane into a reaction liquid to extract, then spin-drying dichloromethane, purifying a product by means of column chromatography, and then spin-drying the product again to obtain cyclopropyl amino acid. The synthetic method is simple, short in reaction step, easy to operate, small in consumption of an organic solvent, simple in post-treatment, high in product purity, small in environmental protection pressure and convenient for industrial production.
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Description

technical field

[0001] The invention relates to a simple preparation method of chiral cyclopropyl amino acid. Background technique

[0002] Cyclopropyl amino acids can be used as biological probes, enzyme inhibitors and original amino acid analogs. The current preparation method is obtained by combining aminocyclopropyl carboxylic acid with 1,2,3,4-tetrahydroquinoline-2-carboxylic acid; this method is cumbersome to operate, the reaction steps are numerous and complicated, and there will be many reactions The production of intermediates affects the reaction yield.

[0003] Many of the properties exhibited by cesium carbonate in organic synthesis originate from the softer Lewis acidity of cesium ions, making it soluble in organic solvents such as alcohols, DMF (N,N-dimethylformamide) and ether. The good solubility in organic solvents enables cesium carbonate to be used as an effective inorganic base to participate in chemical reactions catalyzed by palladium reagents such as...

Claims

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