Preparation method of cefotetan disodium bulk drug

A technology of cefotetan disodium and raw materials, which is applied in the field of preparation of cefotetan disodium raw materials, can solve the problems of long cycle, low product yield and high cost, achieve mild reaction conditions, increase the total yield and Purity, effect of increasing reaction rate and product yield

Active Publication Date: 2021-03-26
SHANDONG LUOXIN PHARMA GRP HENGXIN PHARMA CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The synthesis steps of this method are cumbersome, the cycle is long, the cost is high, and the product yield is relatively low, which is not conducive to large-scale industrial production

Method used

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  • Preparation method of cefotetan disodium bulk drug
  • Preparation method of cefotetan disodium bulk drug
  • Preparation method of cefotetan disodium bulk drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of Compound III

[0028] Add 2,2-dimercaptoacetic acid (2.74g, 0.022mol, molecular weight 124.17) and 15mL ethyl acetate solution in the constant pressure funnel, add compound II 7-MAC (10.5g, 0.02mol, molecular weight 524.61) in the reactor and 60mL ethyl acetate, add the condensing agent CDI (5.19g, 0.032mol, molecular weight 162.15) in batches, stir to dissolve, slowly add the solution in the constant pressure funnel dropwise to the reactor, the reaction temperature is 40°C, the reaction time is 10h, TLC Follow the reaction until the complete disappearance of 2,2-dimercaptoacetic acid, extract the organic phase, dry, filter and concentrate to obtain 12.44g (0.0197mol, molecular weight: 630.77) of compound III, with a yield of 98.6%, HPLC purity of 99.7%, and a maximum of 0.02%.

Embodiment 2

[0030] Preparation of Compound III

[0031] Add 2,2-dimercaptoacetic acid (2.74g, 0.022mol, molecular weight 124.17) and 15mL ethyl acetate solution in the constant pressure funnel, add compound II 7-MAC (10.5g, 0.02mol, molecular weight 524.61) in the reactor and 60mL ethyl acetate, add the condensing agent DCC (6.59g, 0.032mol, molecular weight 206) in batches, stir to dissolve, slowly add the solution in the constant pressure funnel dropwise to the reactor, the reaction temperature is 40°C, the reaction time is 10h, TLC Follow the reaction until the complete disappearance of 2,2-dimercaptoacetic acid, extract the organic phase, dry, filter and concentrate to obtain 12.35 g (0.0195 mol, molecular weight: 630.77) of compound III, the yield is 97.9%, the HPLC purity is 99.6%, and the maximum heterogeneity is 0.02%.

Embodiment 3

[0033] Preparation of Compound III

[0034] Add 2,2-dimercaptoacetic acid (2.74g, 0.022mol, molecular weight 124.17) and 15mL ethyl acetate solution in the constant pressure funnel, add compound II 7-MAC (10.5g, 0.02mol, molecular weight 524.61) in the reactor and 60mL of ethyl acetate, add the condensing agent DIC (4.04g, 0.032mol, molecular weight 126.20) in batches, stir to dissolve, slowly add the solution in the constant pressure funnel into the reactor, the reaction temperature is 40°C, the reaction time is 10h, TLC Follow the reaction until the complete disappearance of 2,2-dimercaptoacetic acid, extract the organic phase, dry, filter and concentrate to obtain 12.11 g (0.0192 mol, molecular weight: 630.77) of compound III, with a yield of 96.6%, HPLC purity of 99.7%, and a maximum of 0.03%.

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Abstract

The invention discloses a preparation method of a cefotetan disodium bulk drug, which comprises the following steps: reacting 7-MAC (II) with 2, 2-dimercaptoacetic acid to prepare a compound III, reacting the compound III with 3-amino-2-formyl -3-oxo sodium propionate to prepare a compound IV, and carrying out deprotection and salification to obtain cefotetan disodium (I). The preparation method is simple and convenient, the reaction conditions are mild, and the obtained cefotetan disodium bulk drug is high in purity and suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a preparation method of cefotetan disodium bulk drug. Background technique [0002] Cefotetan Disodium (Cefotetan Disodium), the chemical formula is C 17 h 15 N 7 Na 2 o 8 S 4 , the molecular weight is 619.59, the chemical name is [6R-(6a, 7a)]-7-[[[4-(2-amino-1-carboxy-2-oxyethylene)-2-(1,3-di Thiobutylcycline)]formyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-sulfur Hetero-l-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid disodium salt. The chemical structure is as follows: [0003] [0004] Cefotetan disodium belongs to the β-lactam antibiotics. β-lactam antibiotics refer to a class of antibiotics with a β-lactam ring in their chemical structure, including penicillins and cephalosporins. This kind of antibiotic has the advantages of broad antibacterial spectrum, strong antibacterial activity, high curative effect, acid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/04C07D501/57
CPCC07D501/04C07D501/57Y02P20/55
Inventor 李军军刘晓彤张德武凌瑜莲侯善波
Owner SHANDONG LUOXIN PHARMA GRP HENGXIN PHARMA CO LTD
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