Synthesis method of cefotaxime acid

A technology of cefotaxamic acid and a synthesis method, applied in the field of medicine and chemical industry, can solve the problems of difficult recovery of dichloromethane and high cost, and achieve the effects of improving product conversion rate and shortening reaction time

Active Publication Date: 2019-08-13
NORTH CHINA PHARMA COMPANY
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is exactly to provide a kind of synthetic method of cefota...

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  • Synthesis method of cefotaxime acid
  • Synthesis method of cefotaxime acid

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Experimental program
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Embodiment 1

[0021] Mix 20.0g of 7-ACA and 26.0g of AE-active ester in a mixed solvent of 100mL of dichloromethane (moisture content: 0.17%) and 20mL of ethanol, add 4mL of purified water and 17mL of triethylamine, and react for 60min. Extract the organic phase twice with water, decolorize, adjust the pH=2.5-3.0 with hydrochloric acid, grow crystals for 1 hour, filter with suction to obtain 37g of cefotaxime acid wet powder, and dry to obtain 33.38g of cefotaxime acid. The purity is 99.5% after testing. , the water content is 0.6%, as shown in Table 1.

Embodiment 2

[0025] Mix 20.0g of 7-ACA and 26.0g of AE-active ester in a mixed solvent composed of 100mL of aqueous dichloromethane (moisture: 0.18%) and 20mL of ethanol, add 4mL of purified water and 17mL of triethylamine, and react with water for 50min. Extract the organic phase twice, decolorize, adjust the pH=2.5-3.0 with hydrochloric acid, grow crystals for 1 hour, filter with suction to obtain 37g of wet cefotaxime acid powder, and dry to obtain 33.66g of cefotaxime acid with a purity of 99.4% and a moisture content of 0.6%. See Table 1.

Embodiment 3

[0027] Mix 20.0g of 7-ACA and 26.0g of AE-active ester in a mixed solvent composed of 100mL of aqueous dichloromethane (moisture: 0.18%) and 20mL of DMF, add 3mL of purified water and 17mL of triethylamine, and react with water for 80min. Extract the organic phase twice, decolorize, adjust pH=2.5-3.0 with hydrochloric acid, grow crystals for 1 hour, filter with suction to obtain 37 g of wet cefotaxime acid powder, and dry to obtain 33.17 g of cefotaxime acid with a purity of 99.3% and a moisture content of 0.7%. See Table 1.

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Abstract

The invention provides a synthesis method of cefotaxime acid. The synthesis method of cefotaxime acid includes the following steps that 1, 7-aminocephalosporanic acid and benzothiazole active ester are added into a mixed solvent composed of aqueous dichloromethane and a cosolvent, and the mixture is stirred to be uniform to obtain a mixed solution; 2, purified water and trimethylamine are added into the mixed solution obtained in step 1, and then acylation reaction is conducted for 50-80 minutes to obtain a reaction solution; 3, water is adopted to conduct extraction on the reaction solution,hydrochloric acid is added into extraction liquid to adjust pH to be 2.5-3.0, and after crystallization, filtration and drying, cefotaxime acid is obtained. According to the method of using quantitative water and aqueous dichloromethane with the water content of 0.1-0.2% for synthesizing cefotaxime acid, aqueous dichloromethane with the water content of 0.1-0.2% is adopted, therefore, the recoverydifficulty of dichloromethane is reduced, the purpose of energy saving is achieved, and cefotaxime acid with high purity is obtained.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and in particular relates to a method for synthesizing cefotaxime acid. Background technique [0002] The chemical name of cefotaxime acid is (6R,7R)-3-[(acetoxy)methyl]-7-[(2-amino-4-thiazolyl)-(methoxyimino)acetamido]- 8-Oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is a third-generation cephalosporin, which is the product of cephalosporin-cefotaxime sodium for injection The main raw material is suitable for pneumonia caused by sensitive bacteria and other lower respiratory tract infections, urinary tract infections, meningitis, sepsis, abdominal infections, pelvic infections of skin and soft tissues, reproductive tract infections, bone and joint infections, etc. [0003] At present, its synthesis method is mainly the AE active ester method. WO9620198 reported the reaction of bis(2-benzothiazole) disulfide (DM) with aminothioxamic acid to obtain AE-active est...

Claims

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Application Information

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IPC IPC(8): C07D501/06C07D501/34
CPCC07D501/06C07D501/34
Inventor 张军立王新辉曹欢刘倩臧飞李小瑞崔克娇
Owner NORTH CHINA PHARMA COMPANY
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