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Method for synthesizing ceftizoxime acid by one-pot method

A technology of ceftizoxamic acid and tetrahydrofuran, which is applied in the field of pharmaceutical and chemical technology synthesis, can solve the problems of complex synthesis steps of ceftizoxamic acid and difficult solvent recovery and application, and achieve the effect of mild process conditions, easy operation and low color grade

Active Publication Date: 2021-02-05
苏州盛达药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The technical problem to be solved by the present invention is to provide a simple and environmentally friendly synthetic method for ceftizoxamic acid in view of the problems in the prior art that the synthesis steps of ceftizoxamic acid are complicated and the solvent is difficult to recycle and apply mechanically

Method used

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  • Method for synthesizing ceftizoxime acid by one-pot method
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  • Method for synthesizing ceftizoxime acid by one-pot method

Examples

Experimental program
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Effect test

Embodiment 1

[0031] (1) Take 40ml of purified water and 130ml of tetrahydrofuran to prepare a solvent, and cool the solvent to below 5°C; add 20g of ANCA (0.10mol), 42g of AE-active ester (0.12mol), and rinse the bottle wall with 10ml of tetrahydrofuran, and control the temperature at 0°C. Add 12.1 g (0.12 mol) of triethylamine and 20 ml of tetrahydrofuran mixture dropwise therein, and finish dropping in 60 minutes at a temperature controlled below 5°C, and react for 4 hours at a temperature controlled at -5°C to 5°C to obtain a reaction liquid; take a small amount of the reaction liquid and use HPLC The residual amount of ANCA was measured by the method, and the residual amount of ANCA in the reaction solution was measured to be 0.29 mg / ml.

[0032] (2) Add 3 mol / L hydrochloric acid solution dropwise to the reaction solution, adjust the pH value of the reaction solution to 2.48, and grow crystals at a temperature of 10-15° C. for 30 minutes.

[0033] (3) Filter the solution in the above s...

Embodiment 2

[0037] (1) Take 40ml of purified water and 170ml of tetrahydrofuran to make a solvent, cool the solvent to below 5°C, add 20g of ANCA (0.10mol), 42g of AE-active ester (0.12mol), rinse with 10ml of tetrahydrofuran, control the temperature at 0°C, and drop into it Add 12.1g (0.12mol) of triethylamine and 20ml of tetrahydrofuran mixed solution, drop it in 60min under temperature control below 5°C, control temperature at -5~10°C, react for 5h to obtain reaction solution; take a small amount of reaction solution and measure ANCA by HPLC method The residual amount of ANCA measured in the reaction solution was 0.41 mg / ml.

[0038] (2) Add 3 mol / L hydrochloric acid solution dropwise to the reaction solution, adjust the pH value of the reaction solution to 2.63, and grow crystals at a temperature of 10-15° C. for 30 minutes.

[0039] (3) Filter the solution in the above step (2) to obtain a filter cake, wash the filter cake with 50ml of tetrahydrofuran, 50ml of purified water, and 100...

Embodiment 3

[0042] (1) Take 40ml of purified water and 90ml of tetrahydrofuran to make a solvent, cool the solvent to below 5°C, add 20g of ANCA (0.10mol), 42g of AE-active ester (0.12mol), rinse with 10ml of tetrahydrofuran, control the temperature at 0°C, and drop into it Add 12.1g (0.12mol) of triethylamine (0.12mol) and 20ml of tetrahydrofuran mixed solution, control the temperature below 5°C in 60min, drop it over 60min, control the temperature at -10~5°C, and react for 5h to obtain the reaction solution; take a small amount of the reaction solution and measure ANCA by HPLC The residual amount of ANCA measured in the reaction solution was 0.48mg / ml.

[0043] (2) Add 3 mol / L hydrochloric acid solution dropwise to the reaction solution, adjust the pH value of the reaction solution to 2.33, and grow crystals at a temperature of 10-15° C. for 30 minutes.

[0044] (3) Filter the solution in the above step (2) to obtain a filter cake, wash the filter cake with 50ml tetrahydrofuran, 50ml pu...

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Abstract

The invention discloses a method for synthesizing ceftizoxime acid by a one-pot method. The method comprises the following steps: reacting 7-ANCA and AE-active ester in a solvent system of water and tetrahydrofuran in the presence of organic alkali, regulating the pH value of the reaction system to 2-3 after the reaction is finished, and carrying out crystal growing, filtering, washing and dryingto obtain the ceftizoxime acid. According to the method, the ceftizoxime acid is synthesized by adopting the one-pot method, the process conditions are mild, an extracting agent does not need to be added for extraction separation, an adsorbent does not need to be added, acid is directly used for neutralization and crystallization after reaction, operation is convenient, and the solvent can be recycled.

Description

technical field [0001] The invention belongs to the technical synthesis field of medicine and chemical industry, and in particular relates to a method for synthesizing ceftizoxamic acid. Background technique [0002] The trade name of Ceftizoxime sodium (Ceftizoxime sodium) is Yibaoshiling or desmethylaminoxime cephalosporin, and its main component and chemical name are (6R,7R)-7-[[2,3-dihydro-2 -imino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2- Carboxylic acid sodium salt, molecular formula: C 13 h 12 N 5 NaO 5 S 2 , molecular weight: 405.38, its structural formula is: [0003] [0004] Ceftizoxime sodium was developed by Tengze Pharmaceutical Co., Ltd. of Japan, and was first listed in Japan in 1982. This product is a semi-synthetic third-generation cephalosporin with a broad antibacterial spectrum, similar to cefotaxime. It has a moderate antibacterial effect on some Gram-positive bacteria and a strong effect on Gram-nega...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/20C07D501/06C07D501/12
CPCC07D501/20C07D501/06C07D501/12
Inventor 杨虎星韩雪英刘玉良缪云峰
Owner 苏州盛达药业有限公司
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