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Method for producing aceclofenac tert-butyl ester

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

Active Publication Date: 2019-10-08
NINGBO SMART PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Method for producing aceclofenac tert-butyl ester

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Embodiment 1

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

Embodiment 2

[0020] Add 500g water in the there-necked flask of 1000ml, start to stir, add 100g (80%, 251.6mmol) diclofenac sodium crude product (DOS5), add 73.6g (377.4mmol, 1.5eq) tert-butyl bromoacetate, 2.9g (17.61mmol , 0.07eq) potassium iodide, 7.7g (22.64mmol, 0.09eq) tetrabutylammonium bisulfate, turn on the heating, raise the temperature to 60°C, start to keep warm, control the temperature at 60-65°C, keep warm for 2.5 hours, slowly cool down to the temperature Keep warm at 5-15°C for half an hour, vacuum filter to obtain a brownish-yellow solid, wash the solid with ethanol 3 times the mass of DOS5 until off-white, and dry at 60°C for 30 hours to obtain 88.7g tert-butyl aceclofenac. The yield is 94.16%, and the liquid phase purity is 99.43%.

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PUM

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Abstract

The invention relates to a method for producing aceclofenac tert-butyl ester. The method includes: allowing diclofenac sodium, tert-butyl bromoacetate, catalyst iodide and tetrabutylammonium hydrogensulfate to have reaction in water, slowly cooling, crystallizing, filtering, washing, and drying. The method is mild in reaction conditions, high in yield, capable of reducing waste liquid discharge,capable of avoiding the toxic effect of organic solvents on human bodies and the like.

Description

technical field [0001] The invention belongs to the field of preparation of aceclofenac tert-butyl ester, in particular to a method for producing aceclofenac tert-butyl ester. Background technique [0002] Now about the synthetic route report of aceclofenac tert-butyl a lot, mainly useful diclofenac sodium and haloacetate tert-butyl in acetone reflux reaction (Qilu pharmaceutical Affairs 2009 Vol.28, No.10) (reaction equation is as follows), have Reflux reaction of diclofenac sodium and tert-butyl chloroacetate in acetonitrile (Jiang Nili, Fan Penggao, Cheng Guohou. Synthesis of aceclofenac [J]. Chinese Journal of Pharmaceutical Industry. 2005 (07).); Diclofenac sodium and tert-butyl chloroacetate Reflux reaction in DMF (Qin Bingchang, Chen Jing, Zhang Youjuan. Synthesis of aceclofenac. China Pharmaceutical Industry Journal, 2008,39(6):408-409.), this type of method has a large amount of organic waste solvent emissions and is difficult to separate Large, the process safety ...

Claims

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Application Information

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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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