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Method for preparing cefuroxime acid

A technology of cefuroxime acid and furoxine, which is applied in the new synthesis field of cefuroxime acid, can solve the problems of cefuroxime acid product discoloration, product purity decline, consumption, etc., and achieves avoiding organic solvent crystallization, less impurity content, and high yield Effect

Active Publication Date: 2010-12-29
国药集团致君(苏州)制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method avoids the disadvantages of the first method, but its two-step yield needs to be improved, especially in the second step crystallization process consumes a large amount of organic solvent, and the organic phase crystallization will coat impurities, resulting in a decrease in product purity. At the same time, the preparation of cefuroxime acid and the problem of discoloration in the product need to be solved

Method used

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  • Method for preparing cefuroxime acid
  • Method for preparing cefuroxime acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] (1) Add 50Kg of phosphorus pentachloride and 450Kg of dichloromethane into a dry reaction kettle and stir, cool to -20°C, add 70Kg of dimethylacetamide dropwise, and add sodium methoxyiminofuranacetate at -15°C 40Kg stirred and reacted for 90min. Add 170Kg of water at a constant temperature of -5°C and stir, then let stand to separate layers. After the organic phase of the lower layer was separated, 10% NaCl aqueous solution was added, stirred, and allowed to stand to separate layers. The organic phase was separated and frozen to -10°C until use.

[0039] (2) 230Kg of pure water, 50Kg of 7-ACA, 0.25Kg of EDTA, and 0.5kg of sodium metabisulfite were stirred at 0°C, and 15% aqueous sodium hydroxide solution was added dropwise to adjust the pH to 8, and stirred until the solid dissolved.

[0040] (3) Add the organic phase prepared in (1) dropwise to the solution prepared in (2), the temperature is controlled at 0° C., and the pH of the reaction solution is maintained at ...

Embodiment 2

[0045] (1) Add 50Kg of phosphorus pentachloride and 450Kg of dichloromethane into a dry reaction kettle and stir, cool to -20°C, add 70Kg of dimethylacetamide dropwise, and add sodium methoxyiminofuranacetate at -15°C 40Kg stirred and reacted for 90min. Add 170Kg of water at a constant temperature of -5°C and stir, then let stand to separate layers. After the organic phase of the lower layer was separated, 10% NaCl aqueous solution was added, stirred, and allowed to stand to separate layers. The organic phase was separated and frozen to -10°C until use.

[0046] (2) 230Kg of pure water, 50Kg of 7-ACA, 0.25Kg of EDTA, and 0.5kg of sodium metabisulfite were stirred at 0°C, and 15% aqueous sodium hydroxide solution was added dropwise to adjust the pH to 9, and stirred until the solid dissolved.

[0047] (3) The organic phase prepared in (1) was added dropwise to the solution prepared in (2), the temperature was controlled at -2°C, and the pH of the reaction solution was maintai...

Embodiment 3

[0052] (1) Add 50Kg of phosphorus pentachloride and 450Kg of dichloromethane into a dry reaction kettle and stir, cool to -20°C, add 70Kg of dimethylacetamide dropwise, and add sodium methoxyiminofuranacetate at -15°C 40Kg stirred and reacted for 90min. Add 170Kg of water at a constant temperature of -5°C and stir, then let stand to separate layers. After the organic phase of the lower layer was separated, 10% NaCl aqueous solution was added, stirred, and allowed to stand to separate layers. The organic phase was separated and frozen to -10°C until use.

[0053] (2) 230Kg pure water, 50Kg 7-ACA, 0.25Kg EDTA, 0.5kg sodium metabisulfite, stir at 0°C, add dropwise 15% sodium hydroxide aqueous solution, adjust pH=8, stir until the solid dissolves.

[0054] (3) Add the organic phase prepared in (1) dropwise to the solution prepared in (2), the temperature is controlled at 0° C., and the pH of the reaction solution is maintained at 6.5 to 7.0 by dropping 15% aqueous sodium hydroxi...

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Abstract

The invention discloses a method for preparing cefuroxime acid. The method comprises the following steps of: performing a chloride acylation reaction on 7-aminocephalosporanic acid (7-ACA) and methoxyiminofuran acetate serving as raw materials; performing deacetylation to synthesize DCCF; performing nucleophilic addition on the DCCF and chlorosulfonyl isocyanate (CSI) serving as a strong carbamoyl reagent to obtain chlorosulfonyl cefuroxime; and hydrolyzing the chlorosulfonyl cefuroxime to obtain cefuroxime acid. In the preparation method, the preparation process is simple, and the cefuroximeacid is crystallized by adopting aqueous solution, so that the loss of organic solvents is reduced; simultaneously, aids are added selectively in the reaction process to improve the quality of products, so that finished products with high purity and yield and good colors are obtained. The purity of the cefuroxime acid prepared by the method is more than 98.5 percent, and the weight yield is approximately 100 percent.

Description

technical field [0001] The invention belongs to the field of drug antibiotics, in particular to a new synthesis method of cefuroxime. Background technique [0002] Cefuroxime acid is a second-generation cephalosporin antibiotic with broad-spectrum antibacterial effect, excellent curative effect on infections caused by most β-lactamase-producing pathogenic bacteria, and effective on the hydrolytic enzymes produced by bacteria that destroy drug action. High stability, thus ensuring excellent antibacterial activity, rarely adverse reactions in clinical application, is currently one of the most widely used cephalosporin antibiotics in clinical practice. [0003] The chemical name of cefuroxime acid is: (6R,7R)-7-[2-furyl(methoxyimino)acetamido]-3-carbamoyloxymethyl-8-oxo-5-thia-1 -Azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. Structure is as shown in formula (I): [0004] [0005] The current production of cefuroxime acid mainly uses 7-aminocaphalosporin acid (7-ACA) as th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/34C07D501/06
Inventor 史利军孙元强
Owner 国药集团致君(苏州)制药有限公司
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