Preparation method of cefuroxime acid

A technology of cefuroxime acid and methoxyiminofuran acetyl chloride dichloromethane, applied in the field of preparation of cefuroxime acid, can solve problems such as poor stability, and achieve the effects of good stability, improved stability and high yield

Active Publication Date: 2021-04-20
QILU ANTIBIOTICS PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Aiming at the problem of poor stability of the existing process, the present invention p...

Method used

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  • Preparation method of cefuroxime acid
  • Preparation method of cefuroxime acid
  • Preparation method of cefuroxime acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] A preparation method suitable for industrial production of cefuroxime acid, comprising the steps of:

[0055] Step (1): Preparation of MDCC

[0056] Add 120g of purified water and 30g of D-7ACA to a clean and dry reaction bottle, control the temperature at 0-10°C, pH ≤ 10, add 20% sodium hydroxide solution dropwise until dissolved, add dichloromethane of methoxyiminofuranacetyl chloride Methane solution, and use 20% sodium hydroxide to control the pH=6.5~7.5 reaction, react until the residue of D-7ACA meets the requirements, separate to obtain the water phase, add 2g of activated carbon, keep warm at 10~20°C, and decolorize for 30 minutes at pH=5.0~7.0, Filter to crystal bottle.

[0057] Add 100ml of dichloromethane to the crystallization bottle, control the temperature at 10-20°C, slowly add dilute hydrochloric acid dropwise to pH = 1.5-2.2, and grow the crystal for 30 minutes. Filter, wash with purified water and dichloromethane. 46.4g of the product was obtained b...

Embodiment 2

[0061] A preparation method suitable for industrial production of cefuroxime acid, comprising the steps of:

[0062] Step (1): Preparation of MDCC

[0063] Add 120g of purified water and 30g of D-7ACA to a clean and dry reaction bottle, control the temperature at 0-10°C, pH ≤ 10, add 20% sodium hydroxide solution dropwise until dissolved, add dichloromethane of methoxyiminofuranacetyl chloride Methane solution, and use 20% sodium hydroxide to control the pH=6.5~7.5 reaction, react until the residue of D-7ACA meets the requirements, separate to obtain the water phase, add 2g of activated carbon, keep warm at 10~20°C, and decolorize for 30min at pH=5.0~7.0, Filter to crystal bottle.

[0064] Add 100ml of dichloromethane to the crystallization bottle, control the temperature at 10-20°C, slowly add dilute hydrochloric acid dropwise to pH = 1.5-2.2, and grow the crystal for 30 minutes. Filter, wash with purified water and dichloromethane. 46.4 g of the product was obtained by dr...

Embodiment 3

[0068] A preparation method suitable for industrial production of cefuroxime acid, comprising the steps of:

[0069] Step (1): Preparation of MDCC

[0070] Add 120g of purified water and 30g of D-7ACA to a clean and dry reaction bottle, control the temperature at 0-10°C, pH ≤ 10, add 20% sodium hydroxide solution dropwise until dissolved, add dichloromethane of methoxyiminofuranacetyl chloride Methane solution, and use 20% sodium hydroxide to control the pH=6.5~7.5 reaction, react until the residue of D-7ACA meets the requirements, separate to obtain the water phase, add 2g of activated carbon, keep warm at 10~20°C, and decolorize for 30min at pH=5.0~7.0, Filter to crystal bottle.

[0071] Add 100ml of dichloromethane to the crystallization bottle, control the temperature at 10-20°C, slowly add dilute hydrochloric acid dropwise to pH = 1.5-2.2, and grow the crystal for 30 minutes. Filter, wash with purified water and dichloromethane. 46.3g of the product was obtained by dry...

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Abstract

The invention relates to a preparation method of cefuroxime acid, wherein the preparation method comprises the following steps: (1) adding D-7ACA into water, and dropwisely adding an alkali solution to dissolve; adding a methoxyimino furan acetyl chloride dichloromethane solution to carry out acylation reaction, layering to obtain a water phase after the reaction is finished, adding activated carbon to decolorize, filtering, then adding dichloromethane, dropwise adding hydrochloric acid to crystallize, filtering and drying to obtain MDCC; and (2) adding MDCC into an organic solvent, adding chlorosulfonyl isocyanate to carry out aminomethyl acylation reaction, and after the reaction is finished, adding pre-cooling water to hydrolyze to obtain a cefuroxime acid suspension; and dropwise adding an alkaline solution for multiple times, growing crystals after dropwise adding is completed each time, finally adjusting the pH value of the system to 1.0-2.0, filtering, and washing to obtain the cefuroxime acid product. The obtained product is good in stability, good in product flowability and easy to subpackage; the crystallization size phase of the product is greatly improved, and the stability is obviously improved.

Description

technical field [0001] The invention relates to a preparation method of cefuroxime acid, belonging to the technical field of medicine synthesis. Background technique [0002] Cefuroxime acid (see formula I) is the intermediate of cefuroxime sodium, and cefuroxime sodium belongs to second-generation cephalosporins. It inhibits cell division and growth by binding to penicillin-binding proteins (PBPs) on the bacterial cell membrane, and finally lyses and kills the bacteria. Cefuroxime has a broad-spectrum antibacterial effect and a wide range of applications. It can be used for respiratory infections caused by sensitive bacteria, ear, nose, throat infections, urinary tract infections, skin and soft tissue infections, bone and joint infections, gonorrhea, including sepsis and Meningeal and other infections. [0003] At present, the processing route of producing cefuroxime acid (see formula I) at home and abroad takes 7-aminocephalosporanic acid (7-ACA) or deacetyl 7-aminocepha...

Claims

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Application Information

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IPC IPC(8): C07D501/06C07D501/12C07D501/34
Inventor 刘军浩王勇进赵振华孙厚斌孙永保李凤侠史韶华徐红梅
Owner QILU ANTIBIOTICS PHARMA
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