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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

Inactive Publication Date: 2017-12-08
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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 Intermediate production, affecting the reaction yield

Method used

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  • Preparation method of chiral cyclopropyl amino acid
  • Preparation method of chiral cyclopropyl amino acid
  • Preparation method of chiral cyclopropyl amino acid

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Experimental program
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Effect test

Embodiment 1

[0038] A total of 30.4 mg (0.1 mmol) of N-(2-formyl-4-methylphenyl)-4-toluenesulfonamide, 25.3 mg (0.1 mmol) of ethyl-2-benzoyl-1-chlorocyclopropanecarboxylic acid ) and 65.2 mg (0.2 mmol) of cesium carbonate were added to 2 mL of N, N-dimethylformamide solvent, and the reaction solution was placed on a magnetic stirrer and stirred at room temperature. Whether the reaction is complete, or a reactant has all reacted, stop the reaction. Add water and dichloromethane to the reaction solution for extraction, add anhydrous sodium sulfate to dry and remove water, filter and take the filtrate, finally add silica gel powder and spin dry dichloromethane, purify the product by column chromatography, and spin dry the solvent again , vacuumized to obtain 41.3mg of cyclopropyl amino acid, yield 82%.

Embodiment 2

[0040] A total of 30.4 mg (0.1 mmol) of N-(2-formyl-4-methylphenyl)-4-toluenesulfonamide, 25.3 mg (0.1 mmol) of ethyl-2-benzoyl-1-chlorocyclopropanecarboxylic acid ) and 65.2 mg (0.2 mmol) of cesium carbonate were added to 2 mL of dimethyl sulfoxide solvent, and the reaction solution was placed on a magnetic stirrer and stirred at room temperature. , or a reactant has all reacted, stop the reaction. Add water and dichloromethane to the reaction solution for extraction, add anhydrous sodium sulfate to dry and remove water, filter and take the filtrate, finally add silica gel powder and spin dry dichloromethane, purify the product by column chromatography, and spin dry the solvent again , vacuumized to obtain 40.2 mg of cyclopropyl amino acid, yield 80%.

Embodiment 3

[0042] A total of 30.4 mg (0.1 mmol) of N-(2-formyl-4-methylphenyl)-4-toluenesulfonamide, 25.3 mg (0.1 mmol) of ethyl-2-benzoyl-1-chlorocyclopropanecarboxylic acid ) and 65.2 mg (0.2 mmol) of cesium carbonate were added to 2 mL of acetonitrile solvent, and the reaction solution was placed on a magnetic stirrer and stirred at room temperature. The reactants have all reacted, stop the reaction. Add water and dichloromethane to the reaction solution for extraction, add anhydrous sodium sulfate to dry and remove water, filter and take the filtrate, finally add silica gel powder and spin dry dichloromethane, purify the product by column chromatography, and spin dry the solvent again , vacuumized to obtain 34.3 mg of cyclopropyl amino acid, yield 68%.

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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.

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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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/16
CPCC07D221/16
Inventor 易英徐云超张方林王洲洲张延飞冯皓唐明
Owner WUHAN UNIV OF TECH
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