Preparation process of 1-mercaptomethyl cyclopropyl acetic acid

A technology of mercaptomethylcyclopropylacetic acid and phenyl, which is applied in the field of preparation technology of 1-mercaptomethylcyclopropylacetic acid, can solve separation difficulties, lower raw material utilization rate, and low ring-opening yield of cyclic sulfides By-products and other problems, to achieve the effect of simplifying the preparation process steps, low cost, and high product yield

Pending Publication Date: 2022-08-02
JIANGSU ALPHA PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Ring-opening yield of cyclic sulfide is low and by-products are easy to form, and separation is difficult, which reduces the utilization rate of raw materials

Method used

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  • Preparation process of 1-mercaptomethyl cyclopropyl acetic acid
  • Preparation process of 1-mercaptomethyl cyclopropyl acetic acid
  • Preparation process of 1-mercaptomethyl cyclopropyl acetic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1 R is benzyl, and acid binding agent is triethylamine

Embodiment 1-1

[0044] Example 1-1 Preparation of compound 3a

[0045] The chemical formula of the reaction is:

[0046] ,

[0047] The compound 4 (11.1 g, 0.1 mol) / dichloromethane (29.5 mL, 0.46 mol) solution was cooled to 0 °C, 5a (i.e. p-toluenesulfonyl chloride, 19.1 g, 0.1 mol), triethylamine (30.5 mL, 0.1 mol) were added. 0.22mol), stir overnight, add water to dilute and separate the organic layer, extract the mixture three times with dichloromethane (50 mL each time), wash the organic matter with saturated sodium chloride (5 mL), and dry the organic matter with anhydrous magnesium sulfate. The organic extract was concentrated under reduced pressure, and the product was purified by recrystallization to obtain compound 3a. The yield in this step was 90.2%.

Embodiment 1-2

[0048] Example 1-2 Preparation of Compound 2

[0049] The chemical formula of the reaction is:

[0050] ,

[0051] A solution of thiourea (22.8 g, 0.3 mol) in 250 ml of absolute ethanol was prepared, compound 3a (0.1 mol) was added to it, refluxed for 30 h, cooled to room temperature, adjusted to pH 5 with 5N HCl, and the solvent was removed in vacuo at room temperature, Extracted twice with 80 ml of dichloromethane, washed the organic layer with saturated sodium chloride, separated and dried with anhydrous sodium sulfate, and distilled under reduced pressure to obtain compound 2. The yield in this step was 89.5%.

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PUM

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Abstract

The invention relates to the technical field of biological pharmacy, in particular to the field of organic synthesis, and more particularly relates to a preparation process of 1-mercaptomethyl cyclopropyl acetic acid. The process comprises the following steps: performing sulfonylation reaction on a raw material 1-hydroxymethyl cyclopropyl acetonitrile under the action of substituted-sulfonyl chloride, performing sulfhydrylation reaction with thiourea, and finally adding alkali to prepare the target product 1-mercaptomethyl cyclopropyl acetic acid. The preparation method disclosed by the invention is low in cost, simple to operate and short in process route, and can meet actual production requirements.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation process of 1-mercaptomethylcyclopropylacetic acid. Background technique [0002] Montelukast sodium, a prescription drug, was developed and produced by Merck & Co., and was approved by the State Food and Drug Administration of China in 1999. Montelukast sodium is an oral leukotriene receptor antagonist that can specifically inhibit the cysteinyl leukotriene (CysLT1) receptor in the airway, thereby improving airway inflammation and effectively controlling asthma symptoms. The chemical name is [R-(E)]-1-[[[1-[3-[2-(7-chloro-2-quinoline)ethenyl]phenyl]-3-[2-(1-hydroxyl -1-methylethyl) phenyl] propyl] sulfur] methyl] sodium cyclopropane acetate, the structural formula is as follows: [0003] . [0004] According to the analysis of the structural formula, 1-mercaptomethylcyclopropylacetic acid or its derivative in the side chain part is the key intermediat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/02C07C323/53C07C335/32C07C303/28C07C309/73
CPCC07C319/02C07C335/32C07C303/28C07C2601/02C07C309/73C07C323/53
Inventor 万新强尹强李昕许鹏仲召亮江涛邱磊陈运动
Owner JIANGSU ALPHA PHARM CO LTD
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