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Sulfonation preparation method of sulfur trioxide halogenated hydrocarbon solution of Ecabet

A technology of sulfur trioxide and ecabet, which is applied in the field of medicine and chemical industry, can solve the problems of low yield and large amount of waste sulfuric acid, and achieve the effects of high yield, less pollution of three wastes, and easy availability of raw materials

Inactive Publication Date: 2018-01-26
CHONGQING KANGLE PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the above disclosed ecabet preparation methods, due to some insufficient factors such as too low yield and too much waste sulfuric acid, it is very necessary to find a high yield and environmentally friendly method

Method used

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  • Sulfonation preparation method of sulfur trioxide halogenated hydrocarbon solution of Ecabet
  • Sulfonation preparation method of sulfur trioxide halogenated hydrocarbon solution of Ecabet
  • Sulfonation preparation method of sulfur trioxide halogenated hydrocarbon solution of Ecabet

Examples

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Effect test

Embodiment 1

[0024] Preparation of ecabet (I)

[0025] Add liquid sulfur trioxide (58.6g, 0.733mol) into 100ml of dichloromethane solvent, mix well, and set aside. Add compound (II) (200g, 0.666mol) and 1000ml of dichloromethane into a three-necked flask, stir until dissolved, cool to 10°C~15°C, add the pre-prepared sulfur trioxide-dichloromethane solution dropwise, stir After reacting for 1.0~1.5h, dichloromethane was concentrated under reduced pressure, and the residue was poured into 400g of ice water, a large amount of off-white precipitate was precipitated, filtered, and the filter cake was dried under reduced pressure to obtain compound (I) as a white solid (HPLC purity>99.0% , yield 90%).

Embodiment 2

[0027] Preparation of ecabet (I)

[0028] Add liquid sulfur trioxide (53.3g, 0.833mol) into 100ml of dichloromethane solvent, mix well, and set aside. Add compound (II) (200g, 0.666mol) and 1000ml of dichloromethane into a three-necked flask, stir until dissolved, cool to 10°C~15°C, add the pre-prepared sulfur trioxide-dichloromethane solution dropwise, stir After reacting for 1.0~1.5h, dichloromethane was concentrated under reduced pressure, and the residue was poured into 400g of ice water, a large amount of off-white precipitate was precipitated, filtered, and the filter cake was dried under reduced pressure to obtain compound (I) as a white solid (HPLC purity>99.0% , yield 84.5%).

Embodiment 3

[0030] Preparation of ecabet (I)

[0031] Add liquid sulfur trioxide (64.0g, 0.799mol) into 100ml of dichloromethane solvent, mix well, and set aside. Add compound (II) (200g, 0.666mol) and 1000ml of dichloromethane into a three-necked flask, stir until dissolved, cool to 10°C~15°C, add the pre-prepared sulfur trioxide-dichloromethane solution dropwise, stir After reacting for 1.0~1.5h, dichloromethane was concentrated under reduced pressure, and the residue was poured into 400g of ice water, a large amount of off-white precipitate was precipitated, filtered, and the filter cake was dried under reduced pressure to obtain compound (I) as a white solid (HPLC purity>99.0% , yield 85%).

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Abstract

The invention discloses a sulfonation preparation method of a sulfur trioxide halogenated hydrocarbon solution of Ecabet. The method is characterized in that dehydroabietic acid (represented by a formula II) is taken as a starting raw material and is sulfonated with the sulfur trioxide halogenated hydrocarbon solution so as to generate Ecabet (represented by a formula I). According to the sulfonation preparation method, the deficiencies of the prior art are overcome; the sulfonation preparation method has the advantages that the sulfonation yield is high, the use amount of sulfur trioxide approximates to a theoretical amount, water is not generated, and a large number of strong-acid waste acid is not generated; and the sulfonation preparation method is simple in operation, safe, environment-friendly and suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical fields of medicine and chemical industry, and in particular relates to a preparation method for sulfonation of sulfur trioxide halogenated hydrocarbon solution of ecabet sodium intermediate ecabet, an anti-digestive canal ulcer drug. Background technique [0002] Anti-peptic ulcer drug Ecabet Sodium (Ecabet Sodium), the chemical name is (+)-(1R,4aS,10aR)-1,2,3,4a,9,10,10a-octahydro-1,4a -Dimethyl-7-(1-methylethyl)-6-sulfonic acid-1-phenanthrene carboxylic acid-6-sodium salt pentahydrate, which belongs to antacid drugs with special curative effect, can be widely used in Gastric ulcer, has a protective effect on gastric mucosal injury between acute gastritis and acute gastritis of chronic gastritis. The drug was first reported in the journals of the American Chemical Society in the 1930s. In the 1980s, Japan’s Tanabe Pharmaceuticals noticed the good efficacy and safety of rosin, and screened out a series of derivat...

Claims

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Application Information

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IPC IPC(8): C07C303/06C07C309/58
Inventor 汤志刚张运辉蔡中文郭栋张朝东费维扬唐洪杨继斌
Owner CHONGQING KANGLE PHARMA
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