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Optically active cyclopropanecarboxamide preparation method

A technology for cyclopropanecarboxamide and optically active substances is applied in the field of preparing cyclopropanecarboxamide optically active substances, and can solve the problems of enzymatic agglomeration, long reaction process, low yield and the like

Inactive Publication Date: 2007-08-01
LIYANG FUX CHEM
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  • Abstract
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Problems solved by technology

But because (S)-dimethylcyclopropane carboxylic acid and (R)-dimethyl cyclopropane carboxylic acid in the above-mentioned method exist in reaction solution simultaneously, therefore also will go through separation (S)-dimethyl cyclopropane carboxylic acid In the process of propane carboxylic acid, a large amount of organic solvent is also used in this separation process
In addition, the (S)-dimethylcyclopropanecarboxylic acid extracted in order to prepare (S)-dimethylcyclopropanecarboxamide also needs to go through the process of reacting with chlorinating reagents and ammonia, so there are long reaction processes and production problems. Low rate and other issues
In addition, when the insoluble ester compound in water undergoes hydrolysis reaction, there will be problems such as coagulation of the enzyme in the reaction

Method used

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  • Optically active cyclopropanecarboxamide preparation method
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  • Optically active cyclopropanecarboxamide preparation method

Examples

Experimental program
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Effect test

preparation example 1

[0072] Preparation of 2,2,2-trifluoroethyl cyclopropanecarboxylate

[0073]

[0074] (S)-Dimethylcyclopropanecarboxylic acid (R)-Dimethylcyclopropanecarboxylic acid

[0075] -2,2,2-trifluoroethyl ester (50%) -2,2,2-trifluoroethyl ester (50%)

[0076] At normal temperature, add 500ml of dichloromethane and 228g of dimethylcyclopropanecarboxylic acid into the reactor, and stir evenly. Under the condition of keeping 20°C, thionyl chloride (SOCl 2 ) 236g. After stirring at room temperature for 1 hour, 190 g of 2,2,2-trifluoroethanol (2,2,2-trifluoroethanol) was slowly added dropwise, followed by stirring at room temperature for 2 hours. with saturated sodium carbonate (Na 2 CO 3 ) solution and washed with anhydrous sodium sulfate (Na 2 SO 4 ) drying and distillation under reduced pressure to remove the organic solvent to obtain dimethylcyclopropanecarboxylic acid-2,2,2-trifluoroethyl ester racemic mixture 340g (87% yield, (S) and (R) configuration each 50 %).

preparation example 2-5

[0078] Preparation of Racemic Mixture of Dimethylcyclopropane Carboxylate

[0079]

[0080] (S)-Dimethylcyclopropanecarboxylate (R)-Dimethylcyclopropanecarboxylate

preparation example

[0081] Each preparation example is distinguished according to the alcohol used: 2,2,2-trichloroethanol (preparation example 2), 2-methoxyethanol (preparation example 3), 2-bromoethanol (preparation example 4), 2-fluoroethanol Ethanol (preparation example 5). Various racemic dimethylcyclopropane carboxylates were prepared according to the procedure described in Preparation 1. The results are shown in Table 1.

[0082] Table 1

[0083] Preparation Example No.

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Abstract

The invention relates to optical active compound by using enzyme, that is cyclopropane carboxamide demonstrated in chemical formula I. The R1 and R2 can be same or different, and are selected from methyl of C1 to C7 from shydrogen- replaced or non replaced straight chain or branched chain; allyl, benzyl group of C1 to C7 from replaced or non-replaced straight chain or branched chain; cycloalkyl of C3 to C7 from replaced or non-replaced straight chain or branched chain; replaced or non-replaced aralkyl or replaced or non-replaced heter aralkyl.

Description

technical field [0001] The invention relates to a method for preparing cyclopropanecarboxamide optically active substances by using enzymes. Background technique [0002] Substituted cyclopropane carboxylic acids (shown in the formula below), especially the optically active 2,2-dimethylcyclopropane carboxylic acid, are chrysanthemum compounds that act as dihydropeptidase I inhibitors and have low mammalian toxicity An important class of substances used in ester series insecticide raw materials (British Patent Publication No. 1260847). In addition, it can also be used as a core intermediate of cilastatin that prevents the decomposition of antibiotics in the kidney (European Patent No. 48301, European Patent No. 48025) and as a chiral resolving agent. Its uses have been widely exploited and are of commercial importance. [0003] [0004] Its original preparation methods include: after using optically active aminos or L-menthol or (S)-mandelic acid with hydroxyl groups to ...

Claims

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Application Information

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IPC IPC(8): C12P13/02C12P41/00
Inventor 李洪求
Owner LIYANG FUX CHEM
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