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Cefuroxime sodium synthesizing method

A technology of cefuroxime sodium and a synthesis method, which is applied in the field of medicine and chemical industry, can solve the problems of easily polluted environment, complicated operation, many side reactions, etc., and achieves the effects of easy availability of raw materials, simple operation and reduction of operation steps.

Inactive Publication Date: 2019-03-12
湖北凌晟药业股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Aiming at problems such as the existing cefuroxime sodium synthesis route with cumbersome steps, complex operation, many side reactions and easy pollution of the environment, the invention provides a synthetic method of cefuroxime sodium

Method used

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  • Cefuroxime sodium synthesizing method
  • Cefuroxime sodium synthesizing method

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Experimental program
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Effect test

Embodiment 1

[0029] A kind of synthetic method of cefuroxime sodium, comprises the steps:

[0030] (1) Dissolve 21.76g (0.08mol) of 7-ACA in 100ml of water in an ice bath at 0-5°C, add dropwise 1mol / L sodium hydroxide solution, adjust the pH to 8.5, and carry out the hydrolysis reaction 2.5 h, to obtain a reaction solution containing D-7-ACA, continue to maintain the temperature at 0-5 ° C, add triethylamine (24.28g, 0.24mol) and trimethylchlorosilane (8.69g, 0.08mol), dropwise add SMIF-Ts Chloroform solution (SMIF-Ts0.096mol, 30ml of chloroform), keep warm for 2.5h, add 20ml of distilled water, separate layers and collect the water phase, adjust the pH to 2.5, crystallize for 2.5h, filter, wash with water until neutral, vacuum at 50°C Dry to obtain DCCF (20.40 g, 80.7%); 1 HNMR(d 6 -DMSO) δ: 9.75 (d, 1H), 7.83 (bs, 1H), 6.69 (m, 2H), 5.60 (s, 1H), 5.02 (d, 1H), 4.73 (m, 2H), 3.90 (s , H), 3.52-3.32 (m, 2H);

[0031] (2) Dissolve 15.80 g of the DCCF in 120 ml of methyl acetate, lower t...

Embodiment 2

[0033] A kind of synthetic method of cefuroxime sodium, comprises the steps:

[0034] (1) Dissolve 21.76g (0.08mol) of 7-ACA in 100ml of water in an ice bath at 0-5°C, add dropwise 1mol / L sodium hydroxide solution, adjust the pH to 9, and carry out the hydrolysis reaction for 2 hours , to obtain a reaction solution containing D-7-ACA, continue to maintain the temperature at 0-5 ° C, add triethylamine (24.28g, 0.24mol) and trimethylchlorosilane (8.69g, 0.08mol), dropwise add SMIF-Ts chloroform Solution (SMIF-Ts0.096mol, 30ml of chloroform), keep warm for 2.5h, add 20ml of distilled water, separate layers and collect the water phase, adjust the pH to 2.3, crystallize for 2h, filter, wash with water until neutral, and dry under vacuum at 50°C. DCCF was obtained (20.96 g, 82.9%);

[0035] (2) Dissolve 15.80 g of the DCCF in 120 ml of methyl acetate, lower the temperature to -10 °C, add CSI (10.61 g, 0.075 mol) dropwise, keep the reaction for 1.0 h, add 30 ml of distilled water, rai...

Embodiment 3

[0037] A kind of synthetic method of cefuroxime sodium, comprises the steps:

[0038] (1) Dissolve 21.77g (0.08mol) of 7-ACA in 100ml of water in an ice bath at 0-5°C, add dropwise 1mol / L sodium hydroxide solution, adjust the pH to 9.5, and carry out the hydrolysis reaction 1.5 h, to obtain a reaction solution containing D-7-ACA, continue to maintain the temperature at 0-5 ° C, add triethylamine (24.28g, 0.24mol) and trimethylchlorosilane (8.69g, 0.08mol), dropwise add SMIF-Ts Chloroform solution (SMIF-Ts0.104mol, chloroform 30ml), keep warm for 2h, add 20ml of distilled water, separate layers and collect the water phase, adjust the pH to 2.0, crystallize for 1.5h, filter, wash with water until neutral, and vacuum dry at 50°C , to obtain DCCF (20.63g, 81.6%);

[0039] (2) Dissolve 15.80g (0.05mol) of the DCCF in 120ml methyl acetate, cool down to -8°C, add CSI (11.32g, 0.08mol) dropwise, keep the reaction for 1.2h, add 30ml distilled water, and heat up to 32°C , reacted for ...

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Abstract

The invention relates to the technical field of pharmaceutical and chemical industries and particularly discloses a cefuroxime sodium synthesizing method. The synthesizing method comprises the steps:dropwise adding alkali solution into 7-aminocephalosporanic acid aqueous solution for hydrolysis reaction, and then subjecting the mixture and (Z)-2-furyl-2-methoxyimino acetic acid p-toluene sulfonicanhydride to amidation to obtain 7-[(Z)-2-furyl-2-methoxyiminoacetamido]-3-hydroxymethyl-4-cephalosporanic acid; dissolving the 7-[(Z)-2-furyl-2-methoxyiminoacetamido]-3-hydroxymethyl-4-cephalosporanic acid into organic solvents to sequentially perform nucleophilic addition and hydrolysis reaction with chlorosulfonyl isocyanate, then adding sodium iso-octoate solution, and performing devitrification, filtering, washing and drying to obtain cefuroxime sodium. According to the synthesizing method, raw materials are wide and easy to obtain, the cost is low, the steps are simple, operation is simple, and side reaction is less.

Description

technical field [0001] The invention relates to the technical field of medicine and chemical industry, in particular to a method for synthesizing cefuroxime sodium. Background technique [0002] Cefuroxime sodium is a highly effective, safe and broad-spectrum second-generation semi-synthetic cephalosporin, which has excellent curative effect on infections caused by most β-lactamase-producing pathogenic bacteria and is currently the most widely used cephalosporin antibiotic in clinical practice one. The structural formula of cefuroxime sodium is as follows: [0003] [0004] The production of cefuroxime sodium now mainly takes 7-ACA (7-aminocephalosporanic acid) as starting raw material, and its synthetic process route mainly comprises as follows: one, carry out the hydrolysis and carbamylation of 3 positions earlier, then carry out 7 However, in the process of condensation between the hydroxymethyl group formed after the hydrolysis of the 3-position and the isocyanate, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/34C07D501/04
CPCC07D501/04C07D501/34
Inventor 金联明何健门万辉邹菁
Owner 湖北凌晟药业股份有限公司
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