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Preparation method of Sarpogrelate intermediate 2-((3-methoxy) phenethyl) phenol

A technology of methoxyphenylacetic acid and sarpogrelate, applied in the field of medicine and chemical industry, can solve problems such as large environmental pollution, and achieve the effects of short process route, low production cost and low cost

Inactive Publication Date: 2012-06-27
PKU HEALTHCARE CORP LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] The present invention overcomes the problem of large environmental pollution in the production of sagrellate intermediate 2-((3-methoxy)phenethyl)phenol in the prior art

Method used

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  • Preparation method of Sarpogrelate intermediate 2-((3-methoxy) phenethyl) phenol
  • Preparation method of Sarpogrelate intermediate 2-((3-methoxy) phenethyl) phenol
  • Preparation method of Sarpogrelate intermediate 2-((3-methoxy) phenethyl) phenol

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Embodiment Construction

[0031] The present invention will be further described below in conjunction with the examples, but it should not be understood that the scope of the subject of the present invention is limited to the following examples. Without departing from the above-mentioned technical idea of ​​the present invention, various replacements and changes made according to common technical knowledge and conventional means in this field shall be included in the scope of the present invention.

[0032] Implementation column 1:

[0033] 1) Preparation of acrylic compound:

[0034] Weigh 16.6 g (0.1 mol) of 3-methoxyphenylacetic acid and 12.2 g (0.1 mol) of salicylaldehyde, add to the reaction flask, dissolve with 40.8 g (0.4 mol) acetic anhydride, then add 25.3 g (0.25 mol) ) triethylamine, heated to 120 ° C for 5 hours, poured into ice water and stirred to precipitate a solid, stood still, and filtered with suction to obtain 2-(3-methoxyphenyl)-3-(2-acetoxyphenyl ) Acrylic acid 26.7g, yield 85....

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Abstract

The invention aims to provide a preparation method of Sarpogrelate intermediate 2-((3-methoxy) phenethyl) phenol (I), which comprises the following steps of: 1) carrying out perkin reaction on 3-methoxyphenylacetic acid (II), salicylic aldehyde (III), organic base and acetic anhydride; 2) further obtaining 2-(3-methoxyphenyl)-3-(2-acetoxy-phenyl) acrylic acid (IV); 3) decarboxylating a compound IV under the existence of quinoline and metal copper to obtain 3-methoxy-2'-acetoxy stilbene (V); 4) hydrolyzing the compound IV to obtain 2-((3-methoxy) styryl) phenol (VI); and 5) carrying out catalytic hydrogenation on the compound IV to obtain a compound I. The technical scheme disclosed by the invention has the characteristics of simplicity in operation, mild reaction condition, no hydroxyl protection or deprotection required, easiness for product purification, short synthetic route, easiness for material obtaining, high yield, low cost and the like and has a wide industrial application prospect.

Description

technical field [0001] The invention relates to the technical field of medicine and chemical industry, in particular to a method for preparing a sagrelorate intermediate. Specifically, it relates to a preparation method of sagrellate intermediate 2-((3-methoxy)phenethyl)phenol, whose chemical structural formula is: [0002] Background technique [0003] Sarpogrelate Hydrochloride, chemical name: (+ / -)-2-(dimethylamino)-1-{[2-(3-methoxyphenyl)phenoxy]methyl}B Succinate monoester hydrochloride. CAS Registry Number: 135159-51-2, the structural formula is as follows: [0004] This drug is a 5-HT2 receptor antagonist and platelet aggregation antagonist developed by Japan's Mitsubishi Pharmaceutical Company. It was first launched in Japan in 1993 and is used to improve ischemic symptoms such as ulcers, pain and cold sensation caused by chronic arterial occlusive disease. [0005] As a key intermediate of sarcogrelate hydrochloride, 2-((3-methoxy)phenethyl)phenol plays a vi...

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Application Information

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IPC IPC(8): C07C43/23C07C41/20
Inventor 柏子辉赵德贺清凯李明川黄白霞
Owner PKU HEALTHCARE CORP LTD
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