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Loxoprofen sodium preparation method

A technology of loxoprofen sodium and loxoprofen acid is applied in the field of preparation of loxoprofen sodium, can solve the problems of many by-products, difficult process control, large environmental pollution, etc. The effect of mild conditions and reasonable price of raw materials

Inactive Publication Date: 2019-04-30
HUBEI XUNDA PHARMA
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

Regarding the synthesis of loxoprofen sodium, in the current bibliographical reports and industrialized production, it is mainly esterified with 2-p-bromomethyl isobenzoic acid and methyl alcohol and then condensed with 2-ethoxycarbonyl cyclopentanone, and then decarboxylated by hydrolysis The product is obtained. This route is currently more recognized, but the route is long, the process is not easy to control, the raw materials are difficult to purchase and expensive, there are many by-products, difficult to separate, the environment is polluted, and the waste liquid is difficult to handle.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The preparation process of loxoprofen sodium is as follows:

[0024] a. Dissolve 1ml of 2-p-bromomethylphenylpropionic acid in 800ml of DMF, then add 1.025ml of 2-ethoxycarbonylcyclopentanone ethyl ester and 1.025ml of sodium hydroxide to it in turn, and react for 8h under normal pressure reflux conditions, Obtain the first intermediate product;

[0025] b. Pour the first intermediate product in the above step a into 300ml water for dilution, then adjust the pH value of the solution to 5-6 with dilute HCL, extract with 900ml toluene three times (300ml each time), and then use 1200ml water three times (each 400ml) washes, separates liquid, gets oil layer, obtains light yellow oil A;

[0026] c. Add 300ml industrial HCL to the light yellow oily substance A obtained in the above step b, stir and reflux for 10h, pour into 300ml water for dilution after cooling to normal temperature, then extract with 900ml toluene three times (300ml each time), and then Wash with water un...

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PUM

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Abstract

The invention discloses a loxoprofen sodium preparation method, which comprises: directly carrying out alkylation on 2-(p-bromomethyl)isophenylpropionic acid as a starting raw material under a NaOH and DMF system, carrying out hydrolysis decarboxylating to obtain a crude product, separating the by-product produced in the reaction through high-vacuum distillation to obtain loxoprofen acid, and carrying out salt forming to obtain the loxoprofen sodium. According to the present invention, the method has characteristics of less synthesis step, mild reaction condition, reasonable price and easy purchase of the raw material, low pollution and low production cost, and is suitable for industrial production, wherein the product content can reach more than 99.8%, and the single impurity is less than0.05%.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of loxoprofen sodium. Background technique [0002] Loxoprofen sodium is a non-steroidal anti-inflammatory drug developed and listed by Sankyo Company in Japan in 1986. Its analgesic effect is significantly better than other propionic acid drugs. Regarding the synthesis of loxoprofen sodium, in the current bibliographical reports and industrialized production, it is mainly esterified with 2-p-bromomethyl isobenzoic acid and methyl alcohol and then condensed with 2-ethoxycarbonyl cyclopentanone, and then decarboxylated by hydrolysis Obtaining the product, this route is relatively recognized at present, but the route is long, the process is difficult to control, raw materials are difficult to purchase and expensive, there are many by-products, difficult to separate, large environmental pollution, and difficult to treat waste liquid. Contents of the invention ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/343C07C69/757C07C51/38C07C51/44C07C65/36C07C51/41
CPCC07C51/38C07C51/412C07C51/44C07C67/343C07C69/757C07C65/36
Inventor 张钜寿吴刚江海洋许广益李亮王运发马路军
Owner HUBEI XUNDA PHARMA
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