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Method for preparing loxoprofen sodium

A compound and reaction technology, applied in the field of loxoprofen sodium preparation technology, can solve the problems of large environmental pollution, long reaction route, unfavorable industrialization, etc., and achieve the effect of strong industrial operation, high purity, and good application prospects

Active Publication Date: 2017-05-24
ZHEJIANG JIUZHOU PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The above traditional techniques all take the product obtained by the condensation of p-bromocresyl propionic acid or its ester and 2-ethoxycarbonyl cyclopentanone as a key intermediate, and then through decarboxylation, salify to obtain loxoprofen sodium; in view of loxoprofen The good drug prospect of profen sodium, it is necessary to develop new process route, to overcome the shortcoming such as reaction route is long, environmental pollution is big, be unfavorable for industrialization in the prior art

Method used

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  • Method for preparing loxoprofen sodium
  • Method for preparing loxoprofen sodium
  • Method for preparing loxoprofen sodium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Embodiment 1: the preparation of 2-(4-methylphenyl) propionic acid (compound 1)

[0063]

[0064]Take a 250ml three-neck flask, add a constant pressure dropping funnel, put magnesium chips (2.70g 112.2mmol) into the reaction flask, and replace it with nitrogen three times for protection. 1-(1-Chloromethyl)-4-methylbenzene (15.76g 102.0mmol) was added into THF (100ml) and mixed evenly, then placed in a constant pressure dropping funnel. Add 1-(1-chloromethyl)-4-methylbenzene / THF (10ml) solution dropwise to the reaction flask at room temperature (20-25°C), turn on magnetic stirring, and the temperature in the reaction flask gradually rises to 50°C. Add the remaining 1-(1-chloromethyl)-4-methylbenzene / THF solution dropwise at 45-50°C. After the dropwise addition is completed, keep the reaction at 45-50°C for 2.0 hours. After the heat preservation is over, lower the temperature to 0°C, and pass carbon dioxide gas into the reaction liquid at 0-5°C until the reaction is ...

Embodiment 2

[0065] Embodiment 2: the preparation of 2-(4-methylphenyl) propionic acid (compound 1)

[0066]

[0067] Take a 250ml three-neck flask, add a constant pressure dropping funnel, put magnesium chips (3.30g 135.8mmol) into the reaction flask, and replace it with nitrogen three times for protection. 1-(1-Chloromethyl)-4-methylbenzene (20.0g 129.3mmol) was added into THF (150ml) and mixed evenly, then placed in a constant pressure dropping funnel. Add 1-(1-chloromethyl)-4-methylbenzene / THF (10ml) solution dropwise to the reaction flask at room temperature (20-25°C), turn on the magnetic stirring, and gradually increase the temperature in the reaction flask to 35°C Quickly transfer the reaction vial to a low temperature bath to cool down to 10°C. Add the remaining 1-(1-chloromethyl)-4-methylbenzene / THF solution dropwise at 10-15°C. After the dropwise addition is completed, keep the reaction at 10-15°C for 1.5h. After the heat preservation is over, lower the temperature to 0°C,...

Embodiment 3

[0068] Embodiment 3: Preparation of 2-(4-methylphenyl) propionic acid (compound 1)

[0069]

[0070] Take a 3000ml three-neck flask, add a constant pressure dropping funnel, put magnesium chips (56.6g 2.33mol) and THF (300ml) into the reaction flask, and replace it with nitrogen three times for protection. 1-(1-Chloromethyl)-4-methylbenzene (300.0g 1.94mmol) was added to THF (1500ml) and mixed evenly, then placed in a constant pressure dropping funnel in batches. Add 1-(1-chloromethyl)-4-methylbenzene / THF (30ml) solution dropwise to the reaction flask at room temperature (20~2-*5°C), turn on the mechanical stirring, and the temperature in the reaction flask gradually rises to After 30°C, quickly transfer the reaction bottle to a low-temperature bath to cool down to 0°C. Add the remaining 1-(1-chloromethyl)-4-methylbenzene / THF solution dropwise at -5~5°C. After the dropwise addition was completed, the mixture was incubated at -5 to 5°C for 1.5 hours. After the heat preser...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a method for preparing loxoprofen sodium. The invention provides a compound with the structure shown in formula 5 and a preparation method and application of the compound, (the formula is defined in the description). The loxoprofen sodium obtained according to the scheme is high in purity, high in industrialized operation, and good in application prospect.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation process of loxoprofen sodium. Background technique [0002] Loxoprofen sodium belongs to phenylpropionic acid non-steroidal anti-inflammatory drugs, first developed by Japan Sankyo Co., Ltd., its chemical name is: 2-[4-(2-oxocyclopentane-1-ylmethyl)benzene Base] sodium propionate, the structural formula is as follows: [0003] [0004] Chinese Journal of Medicinal Chemistry 20 (1) 25-28, 2010, using 4-methylacetophenone as raw material, compound I was obtained through sodium borohydride reduction, and compound I was directly chlorinated without purification to obtain compound II, which was obtained through phase transfer Compound III is obtained by cyanidation in the presence of a catalyst, and compound IV is obtained after compound III is heated, hydrolyzed and acidified under basic conditions. Using benzoyl peroxide as an initiator to initiate the b...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/738C07C51/09C07C59/86C07C67/313C07C69/73C07C67/303C07C67/08C07C51/363C07C57/58C07C51/15C07C57/30
CPCC07C51/09C07C51/15C07C51/363C07C51/412C07C59/86C07C67/08C07C67/303C07C67/313C07C67/343C07C69/738C07C69/73C07C57/58C07C57/30
Inventor 张现毅贺志胡杜芬高红军李原强
Owner ZHEJIANG JIUZHOU PHARM CO LTD
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