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Preparation method of ceftezole and midbody thereof

A technology for ceftazole and intermediates, which is applied in the field of preparation of cephalosporin compounds, can solve the problems of poor product color and purity, low reaction yield and the like, and achieves short reaction time, low cost, and improved yield and purity. Effect

Inactive Publication Date: 2009-09-30
BEIJING SHENKELIANHUA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The method for synthesizing ceftezole in the prior art also has the defects of low reaction yield, product color and luster and poor purity and industrial cost

Method used

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  • Preparation method of ceftezole and midbody thereof
  • Preparation method of ceftezole and midbody thereof
  • Preparation method of ceftezole and midbody thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 5g (16mmol) of 7-ACA was dissolved in 120ml of water, and 3ml of triethylamine was added dropwise to dissolve to prepare a triethylamine solution of 7-ACA for future use. Put 5-mercapto-1,3,4-thiadiazole (4.5g, 38mmol) into a 300ml reaction flask, add 4g of boric acid, 300ml of water, stir to dissolve, heat to 65-70°C, add dropwise 7 - The triethylamine solution of ACA, continue to stir for about 25 minutes after dropping, cool down to 40-50°C, then cool down to 0-5°C, stir for 0.5h, filter, and dry to obtain 5g of solid. It was detected by standard TLC as 7-amino-3-(1,3,4-thiadiazol-5-yl)thiomethyl-2-cephem-2-carboxylic acid.

[0024] Put 5g of 7-amino-3-(1,3,4-thiadiazol-5-yl)thiomethyl-2-cephem-2-carboxylic acid into the reaction flask, add 350ml of water, 300ml of acetone, stir, and then Use triethylamine to adjust the pH to between 7.0 and 7.5, cool down to 0-5°C, slowly add a mixed solution of 1H-tetrazolium-1-acetyl chloride (6.5 g) and acetone (100 ml) dropwise...

Embodiment 2

[0026] 5g (16mmol) of 7-ACA was dissolved in 120ml of water, and 3ml of triethylamine was added dropwise to dissolve to prepare a triethylamine solution of 7-ACA for future use. Put 5-mercapto-1,3,4-thiadiazole (4.5g, 38mmol) into a 300ml reaction flask, add 4g of boric acid, 300ml of water, stir to dissolve, heat to 65-70°C, add dropwise 7 - The triethylamine solution of ACA, continue to stir for about 25 minutes after dripping, cool down to 40-50°C, then cool down to 0-5°C, stir for 0.5h, add 250 ml of acetone to the aqueous solution, stir, and at the same time use triethylamine Adjust the pH to between 7.0 and 7.5, lower the temperature to 0-5°C, slowly add a mixed solution of 1H-tetrazolium-1-acetyl chloride (6.5 g) and acetone (100 ml) dropwise, and maintain the pH at Between 5.6 and 7.0, react for 0.5 hours after dropping, concentrate the acetone, adjust the pH of the aqueous phase to less than 2.5 with 3mol / L hydrochloric acid, and obtain an off-white solid, which is de...

Embodiment 3

[0028] Dissolve 8 g of sodium 7-ACA in 150 ml of water to prepare a sodium 7-ACA solution for later use. Put 5g of 5-mercapto-1,3,4-thiadiazole into a 300ml reaction bottle, add 5g of boric acid and 300ml of water, stir to dissolve, heat to 65-70°C, add 7-ACA sodium solution dropwise while stirring After dropping, continue to stir for about 25 minutes, cool down to 40-50°C, then cool down to 0-5°C, stir for 0.5h, add 250 ml of acetone to the aqueous solution, stir, and adjust the pH to 7.0-7.5 with triethylamine at the same time During this period, the temperature was lowered to 0-5°C, and a mixed solution of 1H-tetrazolium-1-acetyl chloride (6.5 g) and acetone (100 ml) was slowly added dropwise, and the pH was maintained between 5.6 and 7.0 with saturated sodium carbonate solution, and the After completing the reaction for 0.5 hour, concentrate the acetone, and adjust the pH of the aqueous phase to less than 2.5 with 3 mol / L hydrochloric acid to obtain an off-white solid, whi...

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Abstract

The invention relates to a preparation method of a ceftezole and a midbody thereof. The midbody 7-amido-3-(1, 3, 4-thiadiazole-5-base) sulfidomethyl-2-cephem-2-carboxylic acid is prepared from 5-hydrosulphonyl-1, 3, 4-thiadiazole and 7-ACA under certain reaction environment; the prepared midbody 7-amido-3-(1, 3, 4-thiadiazole-5-base) sulfidomethyl-2-cephem-2-carboxylic acid reacts with 1H-tetrazole-1-acetyl chloride to prepare the ceftezole. The ceftezole can be prepared with a one-boiler method in the invention, and the preparation method has the advantages of short reaction time, gentle reaction condition, low cost and suitability of industrial production. In addition, the ceftezolet and the midbody produced by the method have high yield and good purity.

Description

technical field [0001] The present invention relates to a kind of preparation method of cephalosporin compound, especially the preparation method of antibacterial drug ceftezole, and the intermediate 7-amino-3-(1,3,4-thiadiazole-5- Base) the preparation method of thiomethyl-2-cephem-2-carboxylic acid. Background technique [0002] Cephalosporins are the most commonly used antibiotics in clinical practice. The chemical name of ceftezole is: 7-(1H-tetrazol-1-yl)acetamido-3-(1,3,4-thiadiazol-5-yl)thiomethyl-2-cephalosporin En-2-carboxylic acid is a widely used cephalosporin antibiotic. 7-Amino-3-(1,3,4-thiadiazol-5-yl)thiomethyl-2-cephem-2-carboxylic acid is an intermediate of ceftezole. [0003] The preparation method of synthesizing ceftezole intermediate 7-amino-3-(1,3,4-thiadiazol-5-yl)thiomethyl-2-cephem-2-carboxylic acid in industry is roughly divided into four at present Types: weak base catalysis, boron trifluoride catalysis, concentrated sulfuric acid catalysis, tr...

Claims

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Application Information

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IPC IPC(8): C07D501/18C07D501/36
Inventor 申静李泳张典鹏
Owner BEIJING SHENKELIANHUA TECH
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