AE-active ester chemical synthesizing method

A chemical synthesis and active ester technology, applied in organic chemistry, etc., can solve the problems of high synthesis cost, environmental pollution, and ineffective use of by-products, and achieve no three wastes, reduce production costs, great implementation value and social and economic benefits Effect

Inactive Publication Date: 2005-12-21
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In order to overcome the deficiencies in the prior art that the synthetic cost of AE-active ester is high, pollutes the environment, and the by-products are not effectively utilized, the present invention provides an AE-active ester with reasonable process, safe and reliable production, high reaction yield and low production cost. -Chemical synthesis of active esters

Method used

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  • AE-active ester chemical synthesizing method

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Experimental program
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Effect test

Embodiment 1

[0024] The feeding molar ratio is aminothioxime acetic acid: dibenzothiazole sulfide: triphenylphosphine: bis(trichloromethyl) carbonate: pyridine=1:1.2:1.2:0.35:0.5.

[0025] In a 500ml four-neck flask equipped with mechanical stirring, constant pressure dropping funnel, reflux condenser and thermometer, add 20g (0.0995mol) of aminothioxime acetic acid, add dibenzothiazole sulfide, pyridine and 100ml of dichloro Methane, start stirring, slowly add triphenylphosphine 80ml dichloromethane solution dropwise under normal temperature and vigorous stirring, after the addition is complete, stir and react at 20-25°C for 3h (t1), cool in an ice bath, filter, The filter cake was washed with methanol and dried under vacuum to obtain 29.1 g (0.08314 mol, theoretical value 0.0995 mol) of AE-active ester, with a yield of 83.6% and a content of 98.6% (LC); (Trichloromethyl)carbonate in 50ml of dichloromethane solution, after the addition, continue to react at 20-25°C for 3 hours (t2), after...

Embodiment 2

[0027] The feeding molar ratio is aminothioxime acetic acid: dibenzothiazole sulfide: triphenylphosphine: bis(trichloromethyl) carbonate: pyridine=1:1.2:1.2:0.5:1.0.

[0028] In a 500ml four-neck flask equipped with mechanical stirring, a constant pressure dropping funnel, a reflux condenser and a thermometer, add 20g of aminothioxime acetic acid, add dibenzothiazole sulfide (partially recovered, partly newly added), pyridine and 80ml of dichloromethane, start stirring, and slowly dropwise add 70ml of dichloromethane solution of triphenylphosphine (partially recovered, partly newly added) at normal temperature and under vigorous stirring, after the addition is completed, the temperature is raised, and at 25-30°C Stir the reaction at high temperature for 4h (t1), cool in an ice bath, filter, wash the filter cake with methanol, and dry in vacuo to obtain 29.8g (0.085mol) of AE-active ester, with a yield of 85.4% and a content of 98.7% (LC); The filtrate was slowly added dropwise...

Embodiment 3

[0030] The molar ratio of feeding is aminothioxime acetic acid: dibenzothiazole sulfide: triphenylphosphine: bis(trichloromethyl) carbonate: pyridine=1:1.2:1.2:1.5:1.0.

[0031] In a 500ml four-neck flask equipped with mechanical stirring, a constant pressure dropping funnel, a reflux condenser and a thermometer, add 20g of aminothioxime acetic acid, add dibenzothiazole sulfide (partially recovered, partly newly added), pyridine and 100ml of dichloromethane, start stirring, slowly dropwise add 80ml of dichloromethane solution of triphenylphosphine (partially recovered, partly newly added) at normal temperature and under vigorous stirring, after adding, heat up, and Stir the reaction at high temperature for 4h (t1), cool in an ice bath, filter, wash the filter cake with methanol, and dry in vacuo to obtain 28.7g (0.082mol) of AE-active ester, with a yield of 82.4% and a content of 98.1% (LC); The filtrate was slowly added dropwise with 100ml of dichloromethane solution of bis(t...

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Abstract

This invention has offered a chemosynthesis method to AE-activity ester, using ATMAA, dibenzthiazole sulfide, triphenylphosphine as raw materials, in existing of catalyst, after sufficient response of the organic solvent, filter the reaction solution, filter cake is washed and dried to get stated AE-activity ester, join di(trichloromethyl)carbonic acid ester in filtrate, the reaction gets dibenzthiazole and triphenylphosphine, stated benzthiazole sulfide and triphenylphosphine can be recycled after being retrieved. This invention has advanced craft route, rational process conditions, cheap and easy getting raw materials, simple and safe operation.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of AE-active ester. Bis(trichloromethyl)carbonate is used to convert by-products triphenylphosphine and 2-benzothiazole sulfide into raw materials, realizing the recycling of by-products. (2) Background technology [0002] AE-active esters are mainly used in the production of cephalosporin antibiotics. Before the present invention was made, the chemical synthesis method of AE-active ester in the prior art was synthesized from raw materials. Because this method produces a large amount of by-products triphenylphosphine and 2-benzothiazole sulfide, but there is no suitable recovery method, only as waste residue incineration, so the production cost is high, and from the perspective of environmental protection, the pollution problem is serious, the environment The problem is prominent. (3) Contents of the invention [0003] In order to overcome the deficiencies in the prior art that the synthetic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/82
Inventor 苏为科谢媛媛吴登泽
Owner ZHEJIANG UNIV OF TECH
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