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Method for preparing montelukast acid

A montelukast acid and reaction technology, applied in the direction of organic chemistry, etc., can solve the problems of difficult operation, troublesome post-processing, small implementation, etc., and achieve the effects of cheap and easy-to-obtain raw materials and simple reaction operation.

Inactive Publication Date: 2016-02-03
SHANGHAI DESANO CHEM PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It shows that the method is less feasible, and because the ionic liquid that is very easy to absorb water is used, the operation of the reaction is very difficult, and the post-treatment is also troublesome. In addition, the ionic liquid is expensive, so this method is not suitable for industrial production.

Method used

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  • Method for preparing montelukast acid
  • Method for preparing montelukast acid
  • Method for preparing montelukast acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: the preparation of formula III compound

[0036]

[0037] The compound of formula IV (50g, 0.11mol) was dissolved in 200mL of dichloromethane, triethylamine (13.1g, 0.13mol) was added, diphenoxyphosphoryl chloride (32.3g, 0.12mol) was added dropwise at room temperature, and then Stir at room temperature for 2-8 hours, add 250 mL of saturated aqueous sodium bicarbonate solution, extract, collect the organic phase, concentrate under reduced pressure, and dry in vacuo to obtain 68.72 g of the compound of formula III, with a molar yield of 91.2% and an HPLC purity of 99.8% .

Embodiment 2

[0038] Embodiment 2: the preparation of formula III compound

[0039] The compound of formula IV (50 g, 0.11 mol) was dissolved in 200 mL of toluene, 4-dimethylaminopyridine (26.8 g, 0.22 mol) was added, and diphenoxyphosphoryl chloride (32.3 g, 0.12 mol) was added dropwise at room temperature, Stir at room temperature for 2 to 8 hours, add 250 mL of saturated aqueous sodium bicarbonate solution, extract, collect the organic phase, concentrate under reduced pressure, and dry in vacuo to obtain 70.3 g of the compound of formula III, with a molar yield of 92.6%, and an HPLC purity of 99.6%.

Embodiment 3

[0040] Embodiment 3: the preparation of formula I compound

[0041]

[0042] Add the compound of formula II (12.4g, 0.08mol) into 270mL dimethyl sulfoxide, add sodium tert-butoxide (16.3g, 0.17mol) in batches at 20-25°C, stir at room temperature for 0.5-3 hours, and then Add the compound of formula III (45 g, 0.07 mol), then stir the reaction at room temperature for 2 to 8 hours, add water to quench the reaction, extract, collect the organic phase, concentrate under reduced pressure, and dry in vacuo to obtain 37.5 g of the compound of formula I, mol The yield was 98.3%, and the HPLC purity was 99.4%.

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Abstract

The invention discloses a method for preparing montelukast acid. The method comprises a reaction b or a reaction a to a reaction b in the following synthetic route: the formula is shown in the description. The method disclosed by the invention can be used for preparing montelukast acid and salts thereof with low cost and high yield by means of simple operations by using low-cost and easily available raw materials, and is of significance and has practical value to prepare montelukast acid and salts thereof with low cost on a large scale.

Description

technical field [0001] The invention relates to a method for preparing montelukast acid, which belongs to the technical field of medicinal chemistry. Background technique [0002] Montelukast acid or a pharmaceutically acceptable salt thereof can block or inhibit the synthesis and activity of leukotrienes, and it is currently commercially available as a sodium salt. Montelukast acid or sodium salt was first developed and marketed by Merck for the prevention and long-term treatment of asthma in adults aged 15 and over. Its chemical structural formula is shown in Formula I: [0003] [0004] About the preparation of this compound at present, mainly contain following several routes: [0005] The following route is disclosed in European patent EP480717: [0006] [0007] The above-mentioned route is to make 1-(mercaptomethyl)cyclopropyl acetate methyl ester and methanesulfonyl intermediate undergo coupling reaction to obtain methyl ester compound, wherein the hydroxyl of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/18
Inventor 李金亮赵楠王子坤
Owner SHANGHAI DESANO CHEM PHARMA
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