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Optimized impurity removal method for cefuroxime intermediate (3-decarbamoyl-cefuroxime acid)

A technology of carbamoyl and cefuroxime, applied in organic chemistry and other directions, can solve the problems of long drying time, generation of trans impurities, deterioration, etc., and achieve the effects of saving materials, increasing utilization, and reducing costs

Pending Publication Date: 2020-04-03
SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And because 3-decarbamoyl-cefuroxim acid has strong water absorption, the required drying time is longer, and it is in a humid environment after absorbing water, resulting in 3-decarbamoyl-cefururoxime lactone and trans-3- Decarbamoyl-cefuroxime acid rises leading to spoilage
As a result, it is difficult to carry out the next step of production, so the unqualified products in the production process need to be recycled and optimized. In the past, a large amount of water was simply used for washing, and the effect of washing and removing impurities was not good, and trans impurities were produced, and the drying time was long. , and again produce a large amount of internal fat impurities

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Put 20g of impurity-containing 3-decarbamoyl-cefururoxime acid into a 500mL three-neck round-bottomed flask in an ice-water bath at 6°C, then add a mixed solvent of 90g of water, 80g of ethyl acetate, and 1g of ethanol, seal and mix thoroughly for 35 minutes, Stir and mix thoroughly, filter, and filter to remove impurity-containing organic solvents. Then filter the obtained 3-decarbamoyl-cefururoxime acid wet material and put it into a 500mL three-necked round-bottomed flask in an ice-water bath at 9°C, add 30g of water, 75g of ethyl acetate and 75g of dichloromethane mixed solution and stir it fully for 25 minutes, filter Take off 75% mixed solvent. Put the wet material again into a 500mL three-necked round-bottomed flask in an ice-water bath at 7°C, put 80g of dichloromethane into it, stir and mix for 15 minutes, dry in vacuum for 6 hours to remove the solvent, and detect that the moisture content is less than 1% to obtain the product

Embodiment 2

[0030] Put 20g of impurity-containing 3-decarbamoyl-cefururoxime into a 500mL three-necked round-bottomed flask in an ice-water bath at 6°C, then add a mixed solvent of 90g of water, 80g of butyl acetate, and 1.2g of ethanol, and seal and mix thoroughly for 35 minutes , mixed well, filtered, and filtered to remove impurity-containing organic solvents. Then filter the obtained 3-decarbamoyl-cefururoxime acid wet material and put it into a 500mL three-necked round-bottomed flask in an ice-water bath at 9°C, add 30g of water, 75g of butyl acetate and 75g of dichloromethane mixed solution, and fully seal and stir for 25 minutes, filter Remove 80% of the mixed solvent. Put the wet material again into a 500mL three-necked round-bottomed flask in an ice-water bath at 7°C, put 80g of dichloromethane into it, stir and mix for 15 minutes, dry in vacuum for 6 hours to remove the solvent, and detect that the moisture content is less than 1% to obtain the product

Embodiment 3

[0032] Put 20g of impurity-containing 3-decarbamoyl-cefururoxime acid into a 500mL three-necked round-bottomed flask in an ice-water bath at 6°C, then add a mixed solvent of 90g of water, 75g of ethyl acetate, and 1.1g of isopropanol, seal and mix thoroughly After 35 minutes, mix well, filter, and filter to remove impurity-containing organic solvents. Then filter the obtained 3-decarbamoyl-cefururoxime acid wet material and put it into a 500mL three-necked round-bottomed flask in an ice-water bath at 9°C, add 30g of water, 75g of ethyl acetate and 75g of dichloromethane mixed solution, and stir fully for 30 minutes, filter Remove the mixed solvent accounting for 65%. Put the wet material again into a 500mL three-necked round-bottomed flask in an ice-water bath at 8°C, put 80g of dichloromethane into it, stir and mix for 18 minutes, dry in vacuum for 5.5 hours to remove the solvent, and detect that the moisture content is less than 1% to obtain the product

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Abstract

The invention relates to an optimized impurity removal method for cefuroxime intermediate (3-decarbamoyl-cefuroxime acid). The method comprises the following steps: fully stirring and mixing a mixed solvent containing many impurities (mainly being trans-3-decarbamoyl-cefuroxime acid and 3-decarbamoyl-cefuroxime lactone), water, ester and alcohol, removing the solvent, mixing and stirring the obtained material and a mixed solvent of water, ester and dichloromethane, removing the solvent, mixing the obtained material with dichloromethane, and drying the obtained mixture to obtain highly-pure 3-decarbamoyl-cefuroxime acid. The method improves the purity of the cefuroxime intermediate (3-decarbamoyl-cefuroxime acid), so that high-impurity disqualified intermediates are recycled, and the utilization rate of the disqualified intermediates is increased.

Description

technical field [0001] The invention relates to the technical field of production of cephalosporins, in particular to a method for optimizing and removing impurities of a cefuroxime intermediate (3-decarbamoyl-cefururoxime acid). Background technique [0002] 3-decarbamoyl-cefuroxime acid (3-to carbamoyl-cefuroxime acid, CAS number: 56271-94-4, molecular formula: C 15 h 15 N 3 o 7 S, relative molecular mass: 381.361, density: 1.72g / cm 3 ), white crystalline powder, no special smell, is an important intermediate for the production of cefuroxime acid. The structural formula is as follows: [0003] Cefuroxime (English name: Cefuroxime) belongs to the second-generation cephalosporin antibiotics, originally developed and marketed by the British Glaxo Company. Because of its wide application, low metabolism and low toxicity, it is widely used to fight against respiratory, urinary and soft tissue diseases caused by Staphylococcus aureus, Streptococcus, influenza bacillus and ...

Claims

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Application Information

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IPC IPC(8): C07D501/34C07D501/12
CPCC07D501/34C07D501/12
Inventor 马块周忠玉司志杰陈钊王静
Owner SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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