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Low-cost, high-yield 1-(mercaptomethyl)cyclopropylacetic acid production process

A technology of hydroxymethylcyclopropylacetonitrile and cyclopropylacetic acid, which is applied in the field of 1-cyclopropylacetic acid production technology, can solve the problems of high production cost, cumbersome separation and purification steps, unsuitable for industrialization, etc.

Inactive Publication Date: 2019-10-29
上海红蓝医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Aiming at the deficiencies in the prior art, the invention provides a low-cost, high-yield 1-(mercaptomethyl)cyclopropylacetic acid production process, which solves the problem of existing 1-(mercaptomethyl)cyclopropylacetic acid synthesis The production cost of the method is high, most of the intermediates are in liquid state, the separation and purification steps are cumbersome, and it is not suitable for the problems of industrialization defects

Method used

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  • Low-cost, high-yield 1-(mercaptomethyl)cyclopropylacetic acid production process

Examples

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Effect test

Embodiment 1

[0027] In the low-cost, high-yield 1-(mercaptomethyl)cyclopropylacetic acid production process, each raw material includes by weight: 25 parts of 1,1-cyclopropanedimethanol, 7 parts of sodium cyanide, 4 parts of thiourea 2 parts, 2 parts of triethylamine, 2 parts of dichloromethane, 2 parts of thionyl chloride, 2 parts of anhydrous sodium sulfate, 2 parts of sodium iodide, 2 parts of toluene, 2 parts of absolute ethanol and 2 parts of n-heptane.

[0028] S1. Preparation of intermediate cyclopropyl sulfinate: first add 1,1-cyclopropanedimethanol, triethylamine and dichloromethane in the corresponding weight ratio to a 1000mL flask, cool to 3°C in an ice-salt bath and drop Add thionyl chloride, continue to stir at 3°C ​​for 1-2h after dropping, then wash with 300mL of water, then use anhydrous sodium sulfate to dry and filter, the filtrate is evaporated to dryness in a water bath at 35°C under reduced pressure to obtain a white solid as the middle Cyclopropylsulfinate, the conce...

Embodiment 2

[0034] In the low-cost, high-yield 1-(mercaptomethyl)cyclopropylacetic acid production process, each raw material comprises by weight: 20 parts of 1,1-cyclopropanedimethanol, 5 parts of sodium cyanide, 3 parts of thiourea 1 part, 1 part of triethylamine, 1 part of dichloromethane, 1 part of thionyl chloride, 1 part of anhydrous sodium sulfate, 1 part of sodium iodide, 1 part of toluene, 1 part of absolute ethanol and 1 part of n-heptane.

[0035] S1. Preparation of intermediate cyclopropyl sulfinate: First, add 1,1-cyclopropanedimethanol, triethylamine and dichloromethane in the corresponding weight ratio to a 1000mL flask, cool to 0°C in an ice-salt bath and drop Add thionyl chloride, continue to stir at 0°C for 1 hour after dropping, then wash with 200mL of water, then use anhydrous sodium sulfate to dry and filter, and the filtrate is evaporated to dryness in a water bath at 35°C under reduced pressure to obtain a white solid as the intermediate ring Propyl sulfinate, the c...

Embodiment 3

[0041] In the low-cost, high-yield 1-(mercaptomethyl)cyclopropylacetic acid production process, each raw material includes by weight: 30 parts of 1,1-cyclopropanedimethanol, 10 parts of sodium cyanide, 5 parts of thiourea 3 parts, 3 parts of triethylamine, 3 parts of dichloromethane, 3 parts of thionyl chloride, 3 parts of anhydrous sodium sulfate, 3 parts of sodium iodide, 3 parts of toluene, 3 parts of absolute ethanol and 3 parts of n-heptane.

[0042] S1. Preparation of intermediate cyclopropyl sulfinate: first add 1,1-cyclopropanedimethanol, triethylamine and dichloromethane in corresponding weight ratios to a 1000mL flask, cool to 5°C in an ice-salt bath and drop Add thionyl chloride, continue to stir at 5°C for 2 hours after dropping, then wash with 400mL of water, then use anhydrous sodium sulfate to dry and filter, and the filtrate is evaporated to dryness in a water bath at 35°C under reduced pressure to obtain a white solid as the intermediate ring Propyl sulfinate,...

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Abstract

The invention discloses a low-cost, high-yield 1-(mercaptomethyl)cyclopropylacetic acid production process, and relates to the technical field of pharmaceutical production. The low-cost, high-yield 1-(mercaptomethyl)cyclopropylacetic acid production process comprises the following steps that S1, intermediate cyclopropyl sulfinate is prepared, S2, intermediate hydroxymethyl cyclopropyl acetonitrileis prepared, S3, intermediate1-(methanesulfonate)cyclopropyl acetonitrile is prepared, S4, intermediate1(isothioureido) cyclopropyl acetonitrile hydrochloride is prepared, and S5, 1-(mercaptomethyl)cyclopropylacetic acid is prepared. According to the low-cost, high-yield 1-(mercaptomethyl)cyclopropylacetic acid production process, the production efficiency is greatly improved, the energy consumption is reduced, the reaction materials in each step are easy to obtain, the operation is simple, and the low-cost, high-yield 1-(mercaptomethyl)cyclopropylacetic acid production process is suitable for industrial production; and the problem of 1-( mercaptomethyl)cyclopropylacetic acid synthesis is effectively solved, the synthesis cost and sales price of montelukast sodium drug are reduced, the treatment level of asthma is improved, and the construction of domestic medical and health care is accelerated.

Description

technical field [0001] The invention relates to the technical field of medicine production, in particular to a low-cost, high-yield 1-(mercaptomethyl)cyclopropylacetic acid production process. Background technique [0002] Montelukast sodium is as an anti-inflammatory and antiallergic drug with high efficiency, low toxicity and good safety, and 1-(mercaptomethyl) cyclopropyl acetic acid is a key intermediate for the synthesis of montelukast sodium. It contains easily oxidized mercapto groups and more active cyclopropyl groups, and its synthesis has certain difficulties. Nowadays, the synthesis of 1-(mercaptomethyl)cyclopropyl acetic acid has become a difficult and hot research point. [0003] The present invention is based on solving the existing 1-(mercaptomethyl)cyclopropyl acetic acid synthesis method with high production cost, mostly liquid intermediates, cumbersome separation and purification steps, and unsuitability for industrialization. Yield, high-purity 1-(mercapt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/14C07C323/61C07C255/31C07C253/16C07C303/28C07C309/66C07C335/34C07D327/10
CPCC07C253/16C07C303/28C07C319/14C07C335/34C07C2601/02C07D327/10C07C255/31C07C309/66C07C323/61
Inventor 周蕙英
Owner 上海红蓝医药科技有限公司
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