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Method for synthesizing and purifying micafungin

A technology of micafungin and purification method, which is applied in the direction of organic chemistry, can solve the problems of expensive reagents, low product purity, and many waste solvents, and achieve the effect of reducing the generation of waste solvents

Inactive Publication Date: 2017-06-20
JIANGSU SENRAN CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods have defects, the reagents used are all more expensive, and more waste solvents are produced, and the product purity is lower

Method used

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  • Method for synthesizing and purifying micafungin
  • Method for synthesizing and purifying micafungin
  • Method for synthesizing and purifying micafungin

Examples

Experimental program
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Embodiment 1

[0038] The invention provides a technical scheme: a method for synthesizing and purifying a micafungin intermediate, comprising the following steps:

[0039] Add 100ml of dichloromethane, 7.1g (20mmol, 1.0eq) of compound II and 0.2g of pyridine into a 250ml flask, stir to dissolve, raise the temperature to 22°C, add dropwise 3.0g (0.25mol, 1.25eq) of thionyl chloride, and keep for 5 After one hour, after the reaction was completed, concentrate to obtain 8.2 g of oily liquid, continue to add 100 ml of dichloromethane to dissolve, and add 4.0 g of pyridine to stir and cool down to -10°C for later use to obtain a dichloromethane solution of compound III.

[0040] Add 100ml of dichloromethane and 18g (19.1mmol, 1.0eq) of compound IV to a 500ml flask, stir and cool down to -42°C, spray the solution of compound III dropwise, and drop it in 3.5 hours; then keep at -43°C for 8 hour; after the reaction is qualified, the reaction liquid is slowly added dropwise to 100ml of 5% sodium car...

Embodiment 2

[0045] Add 100ml of dichloromethane, 7.1g (20mmol, 1.0eq) of compound II and 0.2g of pyridine into a 250ml flask, stir to dissolve, raise the temperature to 22°C, add 3.6g (0.30mol, 1.50eq) of thionyl chloride dropwise, and keep for 5 One hour later, after the reaction was complete, concentrate to obtain 8.3 g of oily liquid, continue to add 100 ml of dichloromethane to dissolve, and add 4.5 g of pyridine to stir and cool down to -10°C for later use to obtain a dichloromethane solution of compound III.

[0046] Add 100ml of dichloromethane and 18g (19.1mmol, 1.0eq) of compound IV to a 500ml flask, stir and cool down to -45°C, spray and drop the solution of compound III for 3 hours; then keep at -42°C for 8 hour; after the reaction is qualified, the reaction liquid is slowly added dropwise to 100ml of 5% sodium carbonate solution, and stirred at room temperature for 5 hours, left to stand for stratification, and the organic phase is divided, and the aqueous phase is added dropwi...

Embodiment 3

[0050] Add 100ml of dichloromethane, 7.1g (20mmol, 1.0eq) of compound II and 0.2g of pyridine into a 250ml flask, stir to dissolve, raise the temperature to 25°C, add 3.0g (0.30mol, 1.25eq) of thionyl chloride dropwise, and keep for 5 One hour later, after the reaction was complete, concentrate to obtain 8.2 g of oily liquid, continue to add 100 ml of dichloromethane to dissolve, and add 5.0 g of pyridine to stir and cool down to -10°C for use, to obtain a dichloromethane solution of compound III.

[0051] Add 100ml of dichloromethane and 18g (19.1mmol, 1.0eq) of compound IV to a 500ml flask, stir and cool down to -45°C, spray the solution of compound III dropwise, and drop it in 4 hours; then keep at -45°C for 8 hour; after the reaction is qualified, the reaction liquid is slowly added dropwise to 100ml of 5% sodium carbonate solution, and stirred at room temperature for 5 hours, the layers are left to stand, the organic phase is separated, the aqueous phase is added dropwise ...

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Abstract

The invention relates to a method for preparing a pharmaceutical intermediate, in particular to a method for synthesizing and purifying a micafungin intermediate. The method comprises the following steps: subjecting a compound II to a carboxylic acid group acylation reaction to obtain a compound III, subjecting the compound III and a compound IV to a condensation reaction, and carrying out crystallization purification to obtain a high-purity micafungin intermediate I. The preparation method provided by the invention has the advantages of simple process, cheap reagents, low solvent consumption, greatly reduced production cost, and higher purity and yield of products, and easy realization in industrial production.

Description

technical field [0001] The invention relates to the field of preparation methods of pharmaceutical intermediates, in particular to a method for synthesizing and purifying micafungin intermediates. Background technique [0002] Micafungin (Micafungin) is a novel echinocandin antifungal drug obtained by chemical synthesis by transforming the natural product of Coleophoma empetri; Candida krusei and Candida parapsilosis have good inhibitory activity, and also have good inhibitory activity against Aspergillus in vitro, but have no inhibitory activity against Cryptococcus neoformans, Fusarium, Zygomycetes and Trichosporon albajiri. Micafungin (Micafungin) was developed by Fujisawa Corporation of Japan and was launched in Japan in December 2002 under the trade name Fungusrd. It was certified by the US FDA in March 2005 and is currently only approved for the treatment of esophageal candida infection, bone marrow Prevention and treatment of neutropenia in transplant and ADS patient...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14
CPCC07D413/14
Inventor 朱海荀顺义张小容
Owner JIANGSU SENRAN CHEM
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