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Preparation method of cefoxitin

A cefoxitin and acetyl head technology, applied in the field of pharmaceutical chemical synthesis, can solve the problems of insufficient product quality and yield competitiveness, raw materials or process conditions are not suitable for scale-up production, etc., to achieve easy control of product quality and avoid condensation side effects Effects of Response, Good Product Quality and Yield

Inactive Publication Date: 2012-08-15
山东安弘制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] The existing reported literatures all have the problem that the raw materials or process conditions are not suitable for scale-up production, or the product quality and yield are not competitive enough

Method used

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  • Preparation method of cefoxitin

Examples

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Effect test

preparation example Construction

[0051] The preparation method of tert-butyl hypochlorite is synthesized with reference to the synthetic method in "Synthesis and Characterization of New Rubber Chlorinating Agent" (Li Yanli, Shi Shuxian, etc., Journal of Beijing University of Chemical Technology, 31(4):45~49);

[0052] N, N'-dibenzylethylenediamine diacetate was purchased from Shanghai Sinopharm Group Reagent Company, chlorosulfonyl isocyanate was purchased from Shanghai Bangcheng Chemical Company, and methanesulfonic acid was purchased from Shanghai Sinopharm Group Reagent Company.

Embodiment 1

[0054] A preparation method of cefoxitin, comprising the steps of:

[0055] (1) Add 200ml of dichloromethane (organic solvent A) to the aqueous solution 1000ml of the compound of the formula (IV) structure (containing 110g of deacetylcefalotin sodium), and then add 56g of N,N'-dichloromethane at 30°C with temperature control A solution made of benzylethylenediamine diacetate and 800ml of water, the compound of the intermediate formula (III) is precipitated, the temperature is lowered to 0-10°C and stirred for 2 hours; the precipitate is collected by filtration, and the product is washed with water and methylene chloride in turn, Vacuum drying gave 132g of the intermediate compound of formula (III), with a yield of 95.2%;

[0056] through 1 H NMR (400MHz, CDCl 3 ) detection, the results are as follows:

[0057] 1 H NMR (400MHz, CDCl 3 )δ9.02 (d, 1H, J=8.4Hz, CONH), 7.31-7.44 (m, 6H), 6.92-6.96 (m, 2H, thiophene-H), 7.73 (br, 2H, CONH 2 ), 5.53-5.56(dd, 1H), 4.95(d, 1H, J=...

Embodiment 2

[0065] The preparation method of cefoxitin as described in embodiment 1, difference is:

[0066] The organic solvent A described in the step (1) is chloroform, and 128.5 g of the compound of the intermediate formula (III) is obtained, with a yield of 94.9%.

[0067] The compound of intermediate formula (III) structure undergoes 1 H NMR (400MHz, CDCl 3 ) detection, the result is the same as in Example 1.

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Abstract

The invention relates to a preparation method of cefoxitin. The method comprises the following steps: adding a solvent A into a compound aqueous solution with the structure shown in the formula (IV), adding N,N'-dibenzylethylenediamine diacetate or aqueous solution thereof, filtering to obtain a compound with an intermediate structure shown in the formula (III); adding the compound with the intermediate structure shown in the formula (III) into acetone or tetrahydrofuran, adding chloriosulfonyl isocyanate to react, and hydrolyzing; adding acetic ether, filtering, extracting, decoloring, salting out, and filtering to obtain a compound with an intermediate structure shown in the formula (II); adding the compound with the intermediate structure shown in the formula (II) into an organic solvent B, adding organic acid to dissolve, adding a methanol solution with sodium methoxide and tert-butyl hypochlorite to perform methylation reaction, adding sodium pyrosulfite and acetic acid for neutralizing, adding water for extracting, acidifying water phase, filtering to obtain cefoxitin. According to the preparation method, deacetyled cefoxitin always exists in a mode of sodium salt or amine salt, so that the condensation side reaction easily caused by low pH can be avoided, and the product quality and yield can be well controlled.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a preparation method of cefoxitin, and belongs to the technical field of pharmaceutical chemical synthesis. Background technique [0002] Cefoxitin Sodium, chemical name: (6R,7S)-3-carbamoyloxymethyl-7α-methoxy-8-oxo-7β-[2-(2-thienyl) Sodium acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate is a semi-synthetic cephamycin antibiotic developed by Merck Company of the United States, belonging to the second Substitute cephalosporin antibiotics. Cefoxitin sodium has a strong antibacterial effect on Gram-negative bacteria, and its antibacterial spectrum includes Escherichia coli, Klebsiella pneumoniae, indole-positive Proteus and Serratia, Klebsiella, influenza bacillus, Salmonella, and Shigella Wait. It also has a good effect on staphylococcus and various streptococci. Clinically, it is mainly used for respiratory tract infection, endocarditis, peritonitis, pyelonep...

Claims

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Application Information

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IPC IPC(8): C07D501/57
Inventor 许洪飞史韶华汤沸王勇进
Owner 山东安弘制药有限公司
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