Preparation method of descarbamoyl cefuroxime lactone

A technology of acetyl cephalosporin and nitrofloxide, applied in directions such as organic chemistry, can solve the problems of low amount of DCC lactone, inconvenient separation, unfavorable structure analysis and pharmacological research, etc., and achieves the effect of high yield and simple method

Active Publication Date: 2013-01-30
GUANGDONG LIGUO PHARMACY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The amount of DCC lactone produced during the synthesis of cefuroxime acid is very low, which is inconvenient for separation; and there is no synthesis and preparation method for DCC lactone at present, which is not conducive to its structural analysis and pharmacological research.

Method used

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  • Preparation method of descarbamoyl cefuroxime lactone
  • Preparation method of descarbamoyl cefuroxime lactone
  • Preparation method of descarbamoyl cefuroxime lactone

Examples

Experimental program
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Effect test

Embodiment 1

[0028] In a 1000ml four-necked reaction flask, add 70g of DCC and 700ml of acetone, stir well at room temperature (30°C) to dissolve DCC completely, then add 7ml of concentrated sulfuric acid, stir at room temperature (30°C), and a large amount of crystals will precipitate after 10 minutes , maintained stirring, and the reaction was completed after 2.5 hours. The pH value was adjusted to 7.0 with sodium bicarbonate solution, and the precipitate was obtained by filtration, washed successively with acetone, dilute sodium bicarbonate solution and pure water, and then dried at 70°C to obtain 50 g of the target product. The purity (HPLC) of the target product obtained in this embodiment is 99.6%, and the moisture is lower than 1.0%.

Embodiment 2

[0030] In a 1000ml four-necked reaction flask, add 70g of DCC and 700ml of acetonitrile, fully stir at 60°C to dissolve the DCC completely, then add 10.5ml of concentrated hydrochloric acid, reflux and stir at 60°C, a large amount of crystals will precipitate after 5 minutes, keep stirring, After 2 hours the reaction was complete. The pH value was adjusted to 7.2 with sodium bicarbonate solution, and the precipitate was obtained by filtration, washed successively with acetone, dilute sodium bicarbonate solution and pure water, and then dried at 70°C to obtain 60 g of the target product. The purity (HPLC) of the target product obtained in this embodiment is 99.6%, and the moisture is lower than 1.0%.

Embodiment 3

[0032] In a 1000ml four-necked reaction flask, add 70g of DCC, 700ml of DMF and 70ml of acetonitrile, fully stir at 40°C to dissolve the DCC completely, then add 9ml of nitric acid, stir at 40°C, a large amount of crystals are precipitated after 10 minutes, keep stirring, After 2.5 hours the reaction was complete. The pH value was adjusted to 7.0 with sodium bicarbonate solution, and the precipitate was obtained by filtration, washed successively with acetone, dilute sodium bicarbonate solution and pure water, and then dried at 70°C to obtain 54 g of the target product. The purity (HPLC) of the target product obtained in this example is 99.7%, and the moisture is lower than 1.0%.

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Abstract

The invention discloses a preparation method of descarbamoyl cefuroxime lactone. The method includes the steps of: taking descarbamoyl cefuroxime as a raw material, dissolving it in a solvent, and then adding a catalyst to perform an esterification reaction, thus obtaining the descarbamoyl cefuroxime lactone. The preparation method provided in the invention has the advantages of simplicity, easy operation and high yield, and the prepared descarbamoyl cefuroxime lactone has purity not less than 99.5%, thus being convenient for structural analysis and pharmacological study on the descarbamoyl cefuroxime lactone.

Description

technical field [0001] The invention relates to the field of drug synthesis, more specifically, to a preparation method of deacetylcefuroxime lactone. Background technique [0002] Cefuroxime sodium (ester) is developed by Glaxo, and is the most representative product in the second generation of cephalosporin products. Due to its good antibacterial effect, at present, cefuroxime sodium (ester) has entered the national essential drug list and has been marketed in large quantities in China. In the prior art, the synthesis of cefuroxime sodium (ester) usually involves the preparation of the intermediate cefuroxime acid through hydrolysis, urethane acylation reaction, condensation reaction and the like. Wherein, deacetylcefturoxime (DCC) is an intermediate in the synthesis process of cefuroxime acid. [0003] During the synthesis of cefuroxime acid, due to the need to use acid for crystallization, a small amount of DCC reacts with the acid to produce deacetylcefuroxin lactone ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/04
Inventor 曾良兵曾建江
Owner GUANGDONG LIGUO PHARMACY
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