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Preparation method of cefuroxime axetil

A technology of cefuroxime axetil and cefuroxime axetil, which is applied in the field of preparation of cefuroxime axetil, and can solve problems such as difficult control of related substances, low product color grade, unstable quality, etc.

Inactive Publication Date: 2015-12-09
JIANGSU QINGJIANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The disadvantage of this method is that the color grade of the product is low, the related substances are difficult to control, and the quality is unstable.

Method used

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  • Preparation method of cefuroxime axetil

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Implementation example 1 decarbamoyl cephalosporanic acid diphenyl ester is synthesized

[0023] 1L three-neck flask, add 38.1g (0.1mol) decarbamyl cefuroxime acid, 381ml ethyl acetate, 38.1mL DMF, stir and cool to 0-5°C, slowly add 97.5g (0.5mol) diphenyldiazomethane 290mL of ethyl acetate solution, raised to 20-25°C and stirred overnight after addition. Add 380mL of water, stir and separate layers. After separation, the aqueous layer was extracted twice with 75 mL of ethyl acetate, the combined organic phases were washed twice with 380 mL of saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 49.7 g (91%) of the product.

Embodiment 2

[0024] Implementation example 2 cefuroxime diphenylmethyl ester is synthesized

[0025] 1L three-neck flask, add 27.4g (0.05mol) decarbamyl cephalosporanic acid diphenyl ester, 274mL acetone, stir to dissolve, cool to -10°C, slowly add 7.5mL trichloroacetyl isocyanate and 22.5mL The mixed solution of acetone was raised to room temperature and stirred for 2h after the dropwise completion, and the solid was collected and washed with acetone. Transfer the solid into a bottle, add a mixed solution of 5.4g sodium carbonate, 108g water, and 432mL THF, stir at room temperature for 3h, distill off THF under reduced pressure, extract the remaining aqueous solution twice with 275mL ethyl acetate, combine the oil phases, and wash with saturated brine. Dry over sodium sulfate and distill under reduced pressure. The remainder was recrystallized with dichloromethane / n-hexane to obtain 17.1 g of product (58%).

Embodiment 3

[0026] Implementation example 3 cefuroxime acid is synthesized

[0027] Add 20g of cefuroxime diphenylmethyl, 40mL of dichloromethane, 30mL of TFA, 8mL of tertiary methyl ether into a 1L three-necked flask, stir at room temperature for 30min, concentrate under reduced pressure after stirring to remove dichloromethane and TFA, add 80mL of tertiary methyl ether after concentration, After stirring, a solid was precipitated, filtered, washed three times with 40 mL of tertiary methyl ether, and dried to obtain 13.7 g (96%) of the product.

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Abstract

The invention relates to a preparation method of cefuroxime axetil. The preparation method comprises the following steps: (1) reacting de-ammoniated formyl cephalosporanic acid with diphenyl diazomethane to generate acetyl-diphenyl methyl cephalosporanate; (2) reacting diphenyl methyl de-ammoniated formyl cephalosporanate with trichloroacetic isocyanate to generate diphenyl methyl cefuroxime ester; (3) hydrolyzing diphenyl methyl cefuroxime ester to obtain cefuroxime acid; (4) reacting cefuroxime acid with 1-acetoxyl-bromoethane to generate cefuroxime axetil. During the preparation process, the carboxyl group is protected by diphenyl diazomethane, the generation of impurities is reduced, and the product quality is improved.

Description

technical field [0001] The invention relates to medicinal chemistry, in particular to a preparation method of cefuroxime axetil. Background technique [0002] Cefuroxime axetil was successfully developed by the British Glaxo Company. It belongs to the second-generation cephalosporin. It has a broad antibacterial spectrum and strong effect. It has high stability to the hydrolytic enzyme produced by bacteria that destroys the drug effect. Adverse reactions rarely occur and are widely used at home and abroad. [0003] The main synthetic methods reported in literature and patents are: [0004] [0005] The disadvantage of this method is that the color grade of the product is low, the related substances are difficult to control, and the quality is unstable. Contents of the invention [0006] The present invention provides a new synthetic method for the synthesis of cefuroxime axetil to solve the above-mentioned shortcomings, the method reduces the impurity content of the p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/34C07D501/04
CPCY02P20/55C07D501/34C07D501/04
Inventor 何佳汪武卫陈洁刘兴超王栋
Owner JIANGSU QINGJIANG PHARMA
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