New method for preparing cefuroxime sodium compound

A technology of cefuroxime sodium and compounds, applied in the field of chemical synthesis, can solve the problems of low purity of finished products, difficulties in filtration and drying, and difficulty in separation

Active Publication Date: 2010-03-17
灵康药业集团股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The common disadvantage of the second type of method is that 7-ACA is produced by the selective hydrolysis of cephalosporin acetylesterase produced by Crimson yeast fermentation, and 7-DACA is produced. The price of cephalosporin acetylesterase is expensive and the reaction time is long. 7-ACA , 7-DACA in aqueous solution, the four-membered ring lactam bond in its molecular structure is easily hydrolyzed, resulting in easier hydrolysis of the four-membered ring opening at 25 ° C, and the low concentration of the enzymatic hydrolysis substrate makes post-processing very difficult, and the product 7-DACA The fine crystals lead to difficulties in filtration and drying, which is difficult for industrial production. Another disadvantage is that a lactone with properties very close to 7-DACA is formed, which is difficult to separate, resulting in low purity of the finished product

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0031] 1. Deacetyl-7-aminocephalosporanic acid

[0032] Dissolve 272 grams of 7-aminocephalosporanic acid in a mixed solution of 1L methanol and 1L water, stir to lower the temperature, cool to -15°C, add 15% aqueous sodium hydroxide solution dropwise, and control the reaction temperature at -13°C to - 15°C, adjust the pH to 12.5, react for 2 hours, then adjust the pH to 9.5 with 2mol / L hydrochloric acid solution to obtain solution (1).

[0033] 2. 7-[2-(2-furyl)-2-(Z)-(methoxyimino)acetamido]-3-hydroxymethyl-ceph-3-ene-4-carboxylic acid

[0034] Dissolve 600 grams of triphosgene in 1L of toluene, add dropwise to 186 grams of (Z)-methoxyiminofuran acetate ammonium salt and 556 grams of triphenylphosphine in 2L of toluene at 5°C, and keep warm at 5°C React for 3 hours to obtain solution (2); add solution (2) dropwise to solution (1) for mixed reaction, adjust pH=9.5 with 15% sodium hydroxide solution during the reaction, control the reaction temperature at 5°C, add dropwise A...

Embodiment 2

[0038] 1. Deacetyl-7-aminocephalosporanic acid

[0039] Dissolve 136 grams of 7-aminocephalosporanic acid in a mixed solution of 0.5L methanol and 0.5L water, stir to lower the temperature, cool to -13°C, add dropwise 5% aqueous sodium hydroxide solution, and control the reaction temperature at -13°C to -15°C, adjust the pH to 11.5, react for 1 hour, and then adjust the pH to 9.5 with 2 mol / L hydrochloric acid solution to obtain solution (1).

[0040] 2. 7-[2-(2-furyl)-2-(Z)-(methoxyimino)acetamido]-3-hydroxymethyl-ceph-3-ene-4-carboxylic acid

[0041] Dissolve 300 grams of triphosgene in 0.5 L of toluene, add dropwise to 93 grams of (Z)-methoxyiminofuran acetate ammonium salt and 278 grams of triphenylphosphine in 1 L of toluene at 8 ° C, and keep the temperature for 8 ℃ for 2 hours, to obtain solution (2); solution (2) was added dropwise to solution (1) for mixed reaction, and 5% sodium hydroxide solution was used to adjust pH=10 in the reaction, and the reaction temperatur...

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Abstract

The invention relates to a new method for preparing a cefuroxime sodium compound. A target product is prepared by using triphosgene and triphenylphosphine oxide as catalysts, reacting 7-amino-cephalosporanic acid with (Z)-methoxyl imido furylacetic acid ammonium salt and sequentially adding chlorosulfonyl isocyanate and sodium iso-octoate for reaction. The cefuroxime sodium compound prepared by the method is greatly enhanced in purity and yield coefficient and has advantages of inexpensive using materials, simple synthesizing technology and equipment and easy production separation and purification.

Description

technical field [0001] The invention relates to a synthesis method of cephalosporin compounds, in particular to a synthesis method of a new route of cefuroxime sodium compound, which belongs to the technical field of chemical synthesis. Background technique [0002] Cefuroxime sodium, its chemical name is: (6R,7R)-7-[2-furyl(methoxyimino)acetamido]-3-carbamoyloxymethyl-8-oxo-5-sulfur Sodium hetero-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate, molecular formula C 16 h 15 N 4 NaO 8 S, the molecular weight is 446.36, and the structural formula is: [0003] [0004] It is a second-generation cephalosporin antibiotic. Its antibacterial activity against Gram-positive cocci is similar or slightly worse than that of the first-generation cephalosporins, but it is quite stable against the β-lactamase produced by Staphylococcus and Gram-negative bacilli. At present, it is mainly used clinically for various infections caused by sensitive bacteria. [0005] The synthetic method of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/34C07D501/04B01J31/02
Inventor 邱民
Owner 灵康药业集团股份有限公司
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