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Method for preparing aspoxicillin

A technology of apicillin and amoxicillin, applied in the field of drug synthesis, can solve the problem of low yield of deprotection groups, and achieve the effects of less impurities, high yield and short reaction period

Inactive Publication Date: 2020-01-03
黄焕军
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This route still uses 2-nitrobenzene sulfur chloride, and the yield of the final deprotection group is not high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Put 30g of amoxicillin and 150ml of dichloromethane into a 500ml three-necked bottle, cool down to -10°C, add 3eq of triethylamine and 2.2eq of iodotrimethylsilane dropwise at the same time, raise the temperature to 0°C for reaction 3h, compound Ⅰ was obtained.

[0016] Put 1.2eq of Deng potassium salt, 100ml of dichloromethane and 0.3eq of N-methylmorpholine into a 250ml three-neck flask, cool down to -5°C, add 1.3eq of ethyl chloroformate dropwise, and keep the reaction for 5h to obtain Compound II.

[0017] Lower the reaction solution containing compound I to -10°C, slowly add the reaction solution containing compound II dropwise, and keep it warm for 10 hours after the low price is completed. After the reaction, extract the reaction solution with 200ml of water, and then use 100ml of dichloromethane The saturated sodium bicarbonate solution was extracted once, the aqueous layers were combined, and 18% hydrochloric acid was added dropwise to adjust the pH to 4~5. So...

Embodiment 2

[0019] Put 30g of amoxicillin and 150ml of dichloromethane into a 500ml three-necked bottle, cool down to -10°C, add 4eq of triethylamine and 2.3eq of iodotrimethylsilane dropwise at the same time, raise the temperature to 0°C and keep it warm for reaction 3h, compound Ⅰ was obtained.

[0020] Put 1.2eq of Deng potassium salt, 100ml of dichloromethane and 0.3eq of N-methylmorpholine into a 250ml three-necked flask, cool down to -5°C, add 1.2eq of ethyl chloroformate dropwise, and keep the reaction for 5h to obtain Compound II.

[0021] Lower the reaction solution containing compound I to -10°C, slowly add the reaction solution containing compound II dropwise, and keep it warm for 10 hours after the low price is completed. After the reaction, extract the reaction solution with 200ml of water, and then use 100ml of dichloromethane The saturated sodium bicarbonate solution was extracted once, the aqueous layers were combined, and 18% hydrochloric acid was added dropwise to adjus...

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PUM

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Abstract

The invention discloses a method for preparing aspoxicillin, which comprises the following steps of: firstly, protecting the carboxyl group and amino group of amoxicillin, and wherein the potassium Dane salt with ethyl chloroformate is formed into mixed anhydride under the catalysis of N-methylmorpholine, the mixed anhydride is condensed with amoxicillin, and aspoxicillin is obtained after deprotection. The invention has the advantages of simple operation, short reaction period, high yield, high product purity and less impurities, and is suitable for industrial mass production.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, in particular to a method for preparing apoxicillin. Background technique [0002] Compared with other penicillins, apoxicillin has the characteristics of long half-life and low serum protein binding rate. In vitro antibacterial activity studies have shown that it has better broad-spectrum antibacterial activity. Clinically, it can be used to treat secondary infections of sepsis, infective endocarditis, trauma, burns, surgical wounds, pharyngitis, tonsillitis, acute bronchitis, pneumonia and other diseases. The drug is currently in the stage of new drug research and development in my country, and has a good development and application prospect. [0003] Currently, there are three main routes for the synthesis of apoxicillin: [0004] (1) D-aspartic acid-β-carboxamide reacts with the amino-protecting reagent 2-nitrobenzenethiochloride, and then activates the carboxyl group under the actio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D499/68C07D499/12
CPCC07D499/12C07D499/68
Inventor 王存亮许灵艳严学文黄焕军王小桥
Owner 黄焕军
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