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Method for recovering raw materials in preparation process of 7-phenylacetamide-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl

A technology of chloromethyl cephalosporanic acid and p-methoxybenzyl ester, which is applied in the field of raw material recovery, can solve problems such as waste and environmental pollution, achieve the effects of reducing environmental pressure, simple operation, and easy large-scale production

Active Publication Date: 2012-09-26
YILI CHUANNING BIOTECH CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the patents and literatures that have been inquired, there is no recycling post-treatment process for recovering the above-mentioned chemicals. If the waste is discharged, it will generate hundreds of millions of dollars in waste and cause huge pollution to the environment.

Method used

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  • Method for recovering raw materials in preparation process of 7-phenylacetamide-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] A: Take 200g of penicillin sulfoxide, add 1000ml of dioxane and 1000ml of toluene as solvent, 100ml of isopropanol (or ethanol), add 77g of 2-mercaptobenzothiazole at 100°C, after 3 hours of reaction, reduce the pressure to 0.1atm, remove dioxane and toluene, add 1000ml isopropanol to dissolve, add dropwise the pre-dissolved benzenesulfinic acid isopropanol (or ethanol) solution at 35°C, the solution contains 77g sodium benzenesulfinate, drop Add for 2-3 hours, cool down to 0°C, keep warm for 2 hours, filter, wash with isopropanol, and dry to obtain the intermediate of azetidinone sulfinic acid; collect the isopropanol washing solution to obtain the post-treatment alcohol solution;

[0029] Add ethyl acetate corresponding to 50% volume of the alcohol solution under stirring to the alcohol solution obtained after the post-treatment in the above reaction, cool to 0-5°C, a white solid precipitates, filter the solid, and distill the filtrate to remove the solvent, then add ...

Embodiment 2

[0033] A. Take 150g of penicillin sulfoxide ester, add 1100ml of dioxane and 1100ml of toluene each as a solvent, 110ml of isopropanol, add 85g of 2-mercaptobenzothiazole at 90°C, complete the reaction in 4 hours, reduce the pressure to 0.1atm, remove Dioxane and toluene, add 900ml of isopropanol to dissolve, add dropwise the pre-dissolved isopropanol solution of benzenesulfinate at 35°C, the solution contains 90g of sodium benzenesulfinate, add dropwise for 3h, cool down to 0°C, Insulate for 2 hours, filter, wash with isopropanol, and dry to obtain the intermediate of azetidinone sulfinic acid; collect the isopropanol washing solution to obtain the post-treatment alcohol solution;

[0034]Slowly add the alcohol solution obtained after the post-treatment in the above reaction into 8 times the volume of ice water, and a bright yellow solid is precipitated, filtered, dried, and recrystallized with a mixture of 20 parts by volume of petroleum ether and ethyl acetate, of which petr...

Embodiment 3

[0038] A. Take 250g of penicillin sulfoxide, add 900ml of dioxane and 900ml of toluene each as a solvent, 85ml of isopropanol, add 90g of 2-mercaptobenzothiazole at 110°C, and complete the reaction in 3 hours. Reduce the pressure to 0.1atm, remove Dioxane and toluene, add 900ml of isopropanol to dissolve, add dropwise the pre-dissolved benzenesulfinic acid isopropanol solution at 35°C, the solution contains 85g of sodium benzenesulfinate, add dropwise for 2h, cool down to 0°C, Insulate for 2 hours, filter, wash with isopropanol, and dry to obtain the intermediate of azetidinone sulfinic acid; collect the isopropanol washing solution to obtain the post-treatment alcohol solution;

[0039] The alcohol solution obtained after the post-treatment in the above reaction is evaporated to remove the solvent, then added petroleum ether to make a slurry, dispersed and solidified, filtered, and recrystallized with a mixture of 15 to 25 times petroleum ether and ethyl acetate, wherein petro...

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Abstract

The invention provides a method for recovering raw materials in a preparation process of 7-phenylacetamide-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl (GCLE); the recovering method provided by the invention comprises steps of subjecting the obtained solution to certain aftertreatment to recover 2-mercaptobenzothiazole in the aftertreatment of the step of preparation of aza-butanone sulfinic acid intermediates in the technical process of GCLE; and then post-processing layered water phase in the step of preparation of final product GCLE, so as to recover benzene sulfinic acid sodium salt and benzene sulfinic acid amine. The method for recovering raw materials in the preparation process of CCLE is beneficial to mass production, by adopting the method, on one hand, the needed chemical products are recovered, and on the other hand, the pressure to the environment is reduced, so that great economic and social benefits are provided.

Description

technical field [0001] The invention relates to a method for recovering raw materials in the process of preparing 7-phenylacetamide-3-chloromethyl cephalosporanic acid p-methoxybenzyl ester (GCLE for short), in particular to 2-mercaptobenzothiazole in the production process of GCLE , Recovery of sodium benzenesulfinate and ammonium benzenesulfinate. Background technique: [0002] 7-phenylacetamide-3-chloromethyl cephalosporanic acid p-methoxybenzyl ester (GCLE for short) is an important antibiotic raw material, and it is one of the important semi-synthetic antibiotic mother nuclei. Dozens of cephalosporin products can be synthesized using GCLE, especially the third and fourth generation cephalosporin products, such as cefuroxime, ceftazidime, ceftriaxone, cefixime, ceftibuten, etc. [0003] The main steps of the production method related to 7-phenylacetamide-3-chloromethyl cephalosporanic acid p-methoxybenzyl ester (GCLE) are to first oxidize penicillin salt to sulfoxide, t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/72C07D501/24C07C313/02C07C313/06
Inventor 阳海张韬张翔曹晓红文跃强陈媛媛
Owner YILI CHUANNING BIOTECH CO
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