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A kind of preparation method of 3-hydroxymethyl cefotaxime

A technology of hydroxymethyl cefotaxime and cefotaxime, which is applied in the fields of resisting vector-borne diseases, organic chemistry, fermentation, etc., can solve the problems of many steps and complicated operation, and achieve mild reaction conditions, simple and easy-to-control operation, The effect of high product conversion rate

Active Publication Date: 2022-07-12
河北合佳创新医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method is complicated to operate, has many steps, and requires strict process control points.

Method used

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  • A kind of preparation method of 3-hydroxymethyl cefotaxime
  • A kind of preparation method of 3-hydroxymethyl cefotaxime
  • A kind of preparation method of 3-hydroxymethyl cefotaxime

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Example 1: In a 500ml four-necked bottle, add 20g of cefotaxime acid and 160ml of purified water, control the temperature to 25°C to 30°C, stir evenly, add dropwise 3mol / L ammonia solution to adjust the pH to 7.0 to 7.5, and stir for 5min. Add 4g of cephalosporin C deacetylase, continue to use 3mol / L ammonia solution to fine-tune the pH to keep at 7.0-7.5, when the pH value remains unchanged for 5 minutes, the reaction ends, and then filter to remove the cephalosporin C deacetylase, collect filtrate;

[0025] When adjusting the above-mentioned filtrate temperature to 10~15 ℃, add dropwise the mixed solution of 5ml 36% concentrated hydrochloric acid and 7.5ml isopropanol, adjust the pH value to 2.5, crystallize, grow the crystal for 45min and filter, then wash with 30ml purified water. , dried at a drying temperature of 55 ° C and -0.090 MPa for 5 to 10 hours until the moisture content was less than 2.0% to obtain the target product of 3-hydroxymethyl cefotaxime as a pal...

Embodiment 2

[0030] Example 2: In a 500ml four-necked bottle, add 20g of cefotaxime acid and 200ml of purified water, control the temperature to 25°C to 30°C, stir evenly, add 3mol / L ammonia solution dropwise to adjust the pH to 7.0 to 7.5, and stir for 5min Then add 6g of cephalosporin C deacetylase, continue to use 3mol / L ammonia solution to fine-tune the pH to keep at 7.0-7.5, when the pH value remains unchanged for 5 minutes, the reaction ends, and then filter to remove the cephalosporin C deacetylase , collect the filtrate;

[0031]When adjusting the temperature of the above-mentioned filtrate to 10~15 ℃, dropwise add the mixed solution of 6ml 36% concentrated hydrochloric acid and 6ml ethanol, adjust the pH value to 2.0, crystallize, filter after cultivating the crystal for 45min, then wash with 20ml purified water, Vacuum drying at a drying temperature of 50 ° C and -0.095 MPa for 5 to 10 hours until the moisture content is less than 2.0% to obtain the target product of 3-hydroxymet...

Embodiment 3

[0032] Example 3: In a 500ml four-necked bottle, add 20g of cefotaxime sodium and 240ml of purified water, control the temperature to 25°C to 30°C, stir evenly, add 3mol / L ammonia solution dropwise to adjust the pH to 7.0 to 7.5, and stir for 5min After adding 8g of cephalosporin C deacetylase, continue to use 3mol / L ammonia solution to fine-tune the pH to keep at 7.0-7.5, when the pH value remains unchanged for 5 minutes, the reaction ends, and then filter to remove the cephalosporin C deacetylase , collect the filtrate;

[0033] When the temperature of the filtrate was adjusted to 10-15°C, a mixed solution consisting of 4ml of 85% phosphoric acid and 8ml of methanol was added dropwise, and the pH value was adjusted to 4.0 for crystallization. Vacuum drying at a temperature of 60 ° C and -0.085 MPa for 5 to 10 hours until the moisture content is less than 2.0% to obtain the target product of 3-hydroxymethyl cefotaxime as a pale yellow powder. The mass yield of the target prod...

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Abstract

The invention discloses a preparation method of 3-hydroxymethyl cefotaxime, which is characterized by comprising the following steps: adding cefotaxime to purified water at room temperature, adjusting the pH, adding cephalosporin C deacetylase, and maintaining the pH when the pH is maintained. When unchanged, the cephalosporin C deacetylase is filtered off, the filtrate is collected, the mixed solution of an inorganic acid and an organic solvent is added dropwise, the pH is adjusted to crystallize, the crystal is grown, filtered, and dried to obtain 3-hydroxymethylcefotaxime. The invention uses cefotaxime as raw material, adopts biological enzyme method, avoids the use of chemical synthesis methods, has few types of solvents, low toxicity and environmental protection, mild reaction conditions, simple steps, high product conversion rate, and simple and easy-to-control operations. The yield of the target product can reach 74%, and the purity can reach up to 97.6%. It fills the blank of preparing the impurity by biological enzymatic synthesis method, which is beneficial to the subsequent structure analysis and pharmacological research, and has important theoretical significance and practical application value for improving the quality of cefotaxime sodium and reducing the risk of clinical drug use.

Description

technical field [0001] The invention relates to biological and pharmaceutical raw materials and intermediates, and more particularly, to a method for synthesizing and preparing 3-hydroxymethyl cefotaxime, a key known impurity in the quality research of cefotaxime sodium. Background technique [0002] Cefotaxime sodium is a third-generation semi-synthetic cephalosporin whose chemical name is (6R,7R-3-[(acetoxy)methyl]-7-[(2-amino-4-thiazole) base)-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate, sodium salt, which was manufactured by Germany Jointly developed by Hoechst and French Roussel Company, it was successfully developed in 1977 and launched in 1980. Its powder injection is named Claforan, which has the characteristics of broad-spectrum, high efficiency, enzyme resistance, and small side effects. It is clinically used in various sensitive bacteria. Infection treatment. [0003] Most of the synthetic routes of cefotaxime sodium at home ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P35/02C07D501/34C07D501/12
CPCC12P35/02C07D501/34C07D501/12Y02A50/30
Inventor 雷影孙收杰陈芳芳赵威朱敬华
Owner 河北合佳创新医药科技有限公司
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