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Method for preparing cefuroxime acid

A technology of cefuroxime acid and cephalosporanic acid, which is applied in the direction of organic chemistry, can solve the problems of restricting industrial production, and achieve the effects of less discharge of three wastes, simple process operation and high yield

Active Publication Date: 2011-06-15
蚌埠丰原涂山制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this approach generally adopts the acid chloride method to introduce (cis)-2-(2-furyl)-2-(methoxyimino)acetic acid (SMIFA) at the C7-position of 7-DACA, which limits the its industrial production

Method used

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

Examples

Experimental program
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Embodiment 1

[0030] Add 550ml of methanol and 550ml of purified water into the reaction flask to form a mixed solvent, then add 100g of 7-ACA, stir and cool down to -15°C, add 15% sodium hydroxide purified aqueous solution dropwise, control the temperature at -15°C, and pH at 11 Under the condition of ~12, carry out selective hydrolysis reaction; HPLC detects that 7-ACA peak completely disappears as the reaction end point, and the reaction time is about 1 hour; DACA solution is kept at low temperature for use;

[0031] Add 80 ml of Et to the above 7-DACA solution 3 N, 118.4g 2-[2-furyl]-2-[methoxyimino]acetic acid-(2,5-dioxo-pyrrolidinyl)-1-ester, reaction under ice-water bath conditions, HPLC detection 7 - DACA residual area < 1% is the reaction end point; after the reaction is completed, separate the water phase, add 6g of activated carbon and stir for half an hour to decolorize; then filter, wash with water, cool down to 5°C, add 2mol / L hydrochloric acid dropwise to pH = 2, keep warm ...

Embodiment 2

[0034] Add 300ml of ethanol, 300ml of methanol, and 600ml of purified water into the reaction flask to form a mixed solvent, then add 100g of 7-ACA, stir and cool down to 0°C, add 15% potassium hydroxide purified aqueous solution dropwise, control the temperature to 0°C, and the pH to 11-12, carry out selective hydrolysis reaction; HPLC detects that the 7-ACA peak completely disappears as the reaction end point, and the reaction time is about 1 hour; after the reaction is completed, add 2mol / L hydrochloric acid dropwise to adjust the pH to 7.0-8.0 to obtain a 7-DACA solution low temperature standby;

[0035] Add 100 ml of Et to the above 7-DACA solution 3 N, 146.5g 2-[2-furyl]-2-[methoxyimino]acetic acid-(2,5-dioxo-pyrrolidinyl)-1-ester, reaction under ice-water bath conditions, HPLC detection 7 - DACA residual area < 1% is the reaction end point; after the reaction is completed, separate the water phase, add 6g of activated carbon and stir for half an hour to decolorize; the...

Embodiment 3

[0038] Add 600ml of isopropanol and 600ml of purified water into the reaction flask to form a mixed solution, then add 100g of 7-ACA, stir and cool down to -15°C, add 30% sodium hydroxide purified aqueous solution dropwise, control the temperature at -15°C, pH The value is 11~12, carry out selective hydrolysis reaction; HPLC detects that 7-ACA peak completely disappears as the reaction end point, and the reaction time is about 1 hour; DACA solution is kept at low temperature for use;

[0039] Add 110 ml of Et to the above 7-DACA solution 3 N, 160.5g 2-[2-furyl]-2-[methoxyimino]acetic acid-(2,5-dioxo-pyrrolidinyl)-1-ester, reaction under ice-water bath conditions, HPLC detection 7 - DACA residual area < 1% is the reaction end point; after the reaction is completed, separate the water phase, add 6g of activated carbon and stir for half an hour to decolorize; then filter, wash with water, cool down to 5°C, add 2mol / L hydrochloric acid dropwise to pH = 2, keep warm Stir for 2 ho...

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Abstract

The invention provides a method for preparing cefuroxime acid. The method comprises the following steps: (1) selectively hydrolyzing 7-aminocephalosporanic acid (7-ACA) with aqueous alkali so as to obtain 3-deacetylation-7-aminocephalosporanic acid (7-DACA); (2) condensing 2-(2-furyl)-2-(methoxyimino)acetic acid-(2,5-dioxo-pyrrolidyl)-1-ester and 7-DACA so as to obtain 3-decarbamyl-cefuroxime acid (DCCF); and (3) modifying 3-hydroxymethyl of DCCF with chlorosulfonyl isocyanate so as to obtain the cefuroxime acid. In the method, low-temperature selective hydrolysis is carried out by using inorganic base to remove the 3-ester group of 7-ACA so as to prepare 7-DACA; C7-amino modification is carried out by an active ester method so as to obtain DCCF; and the 3-hydroxymethyl of DCCF is modified into carbamoyl methoxyl so as to obtain the cefuroxime acid. The method has the advantages of less emission of three wastes and high yield, is simple and convenient to operate, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing cefuroxime acid, which belongs to the field of drug synthesis. Background technique [0002] Cefuroxime series belongs to the second-generation cephalosporins, which have broad-spectrum antibacterial effect, not only have strong antibacterial activity against Gram-positive cocci, but also have good antibacterial activity against some Gram-negative bacteria, especially in In the treatment of mixed infections of Gram-positive and Gram-negative bacteria, the drug is preferred. It has high stability to the hydrolytic enzyme produced by bacteria that destroys the drug effect, and rarely causes adverse reactions in clinical applications. [0003] Cefuroxime was first successfully developed and patented by Glaxo Wellcome. The product was first launched in the UK, Ireland, Germany and Italy in 1978 under the trade name "Xilixin", and was subsequently sold in many countries and regions around the world. It was ...

Claims

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Application Information

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IPC IPC(8): C07D501/34C07D501/04
Inventor 汪洪湖
Owner 蚌埠丰原涂山制药有限公司
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