A kind of method for producing aceclofenac tert-butyl ester

A technology of aceclofenac and tert-butyl bromoacetate, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problem of large discharge of organic waste solvents, low process safety factor, and difficult product separation and other issues, to achieve the effect of sufficient response, process safety and good application prospects

Active Publication Date: 2022-07-22
NINGBO SMART PHARMA
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Problems solved by technology

[0004] The technical problem to be solved by this invention is to provide a kind of method of producing aceclofenac tert-butyl ester, to overcome the large discharge of organic waste solvent, the difficulty of product separation and the Defects with low process safety factor

Method used

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  • A kind of method for producing aceclofenac tert-butyl ester

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Embodiment 1

[0018] Add 100g of water to a 250ml three-necked flask, turn on stirring, add 20g (80%, 50.31mmol) of crude diclofenac sodium (DOS5), add 16.7g (85.64mmol, 1.7eq) of tert-butyl bromoacetate, 0.6g (3.614mmol) , 0.07eq) potassium iodide, 1.6g (4.713mmol, 0.09eq) tetrabutylammonium hydrogen sulfate, turn on the heating, heat up to 60 ℃, start to keep warm, control the temperature at 60-65 ℃, keep warm for 2 hours, slowly cool down to the temperature The temperature was 5-15°C, kept at 5-15°C for half an hour, and vacuum filtered to obtain a brownish-yellow solid. The solid was washed with ethanol 3 times the mass of DOS5 until off-white, and dried at 60°C for 30 hours to obtain 17.3 g of aceclofenac tert-butyl ester. The yield was 94.5%, and the liquid phase purity was 99.62%.

Embodiment 2

[0020] Add 500g of water to a 1000ml three-necked flask, turn on stirring, add 100g (80%, 251.6mmol) of crude diclofenac sodium (DOS5), add 73.6g (377.4mmol, 1.5eq) of tert-butyl bromoacetate, 2.9g (17.61mmol) , 0.07eq) potassium iodide, 7.7g (22.64mmol, 0.09eq) tetrabutylammonium hydrogen sulfate, turn on the heating, heat up to 60 ℃, start to keep warm, control the temperature at 60-65 ℃, keep warm for 2.5 hours, slowly cool down to the temperature The temperature was 5-15°C, kept at 5-15°C for half an hour, and vacuum filtered to obtain a brownish-yellow solid. The solid was washed with ethanol 3 times the mass of DOS5 to off-white, and dried at 60°C for 30 hours to obtain 88.7 g of aceclofenac tert-butyl ester. The yield was 94.16%, and the liquid phase purity was 99.43%.

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Abstract

The invention relates to a method for producing aceclofenac tert-butyl ester. The method comprises: reacting diclofenac sodium, tert-butyl bromoacetate, catalyst iodide and tetrabutylammonium hydrogen sulfate in water, slowly cooling down, crystallizing, filtering, washing and drying. The method has the advantages of mild reaction conditions, high yield, reduced discharge of waste liquid, and avoidance of toxic effects of organic solvents on human body.

Description

technical field [0001] The invention belongs to the field of preparation of aceclofenac tert-butyl ester, and particularly relates to a method for producing aceclofenac tert-butyl ester. Background technique [0002] Now there are many reports on the synthetic route of tert-butyl acetochlorophenate, mainly the reflux reaction of diclofenac sodium and tert-butyl haloacetate in acetone (Qilu pharmaceutical Affairs 2009 Vol.28, No.10) (the reaction equation is as follows), there are Reflux reaction of diclofenac sodium and tert-butyl chloroacetate in acetonitrile (Jiang Nili, Fan Penggao, Cheng Guohou. Synthesis of aceclofenac [J]. China Pharmaceutical Industry Journal. 2005(07).); Diclofenac sodium and tert-butyl chloroacetate Reflux reaction in DMF (Qin Bingchang, Chen Jing, Zhang Youjuan. Synthesis of Aceclofenac. Chinese Journal of Pharmaceutical Industry, 2008, 39(6): 408-409.), this type of method has a large discharge of organic waste solvents and is difficult to separat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C227/18C07C227/42C07C229/42
CPCC07C227/18C07C227/42C07C229/42
Inventor 王闯向永强殷智德顾启航刘书君肖然
Owner NINGBO SMART PHARMA
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