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Industrial production method for cyclopropyl sulfinate

A technology of cyclopropyl sulfinate and ester compound, which is applied in the synthesis of pharmaceutical intermediates and in the field of industrial production of montelukast sodium intermediate cyclopropyl sulfinate, which can solve the problem of low yield of final product and unfavorable Industrialized production, high temperature of cyclization reaction, etc., to achieve the effect of facilitating industrialized production, solving the difficulty of product filtration, and high product yield and purity

Inactive Publication Date: 2011-10-05
江苏八巨药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method has few reaction steps, short process route and low raw material price, this method not only extracts the intermediate product cyclic sulfite and then carries out the next step reaction, the cyclization reaction temperature is higher, and the final product yield is lower, and Direct filtration, low product quality, not conducive to industrial production

Method used

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  • Industrial production method for cyclopropyl sulfinate
  • Industrial production method for cyclopropyl sulfinate
  • Industrial production method for cyclopropyl sulfinate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Put 100ml of toluene into the reaction bottle, then add 50g of dibromoneopentyl glycol, stir and heat up to 45°C, during the dropwise addition, keep the temperature at 45°C-55°C, and start to add 25g of thionyl chloride dropwise. During the dropwise addition, dibromoneopentyl glycol gradually dissolves, and hydrogen chloride gas is generated, and the generated hydrogen chloride gas is absorbed with water. After the dropwise addition, the temperature was controlled at 45° C. to 55° C. and kept for 3.0 hours. During the heat preservation process, samples were taken and analyzed by TLC. After the raw materials were completely reacted, the temperature was controlled below 70°C, and the solvent was recovered under reduced pressure until evaporated to dryness. After evaporating to dryness, 10 g (about 10 ml) of DMF was added to the residue to obtain 70 g of esterified compound II / DMF mixture. Wherein the developer used for TLC detection is a mixed developer of petroleum ethe...

Embodiment 2

[0043] Put 100ml of xylene into the reaction bottle, then add 50g of dibromoneopentyl glycol, stir and heat up to 50°C, during the dropwise addition, keep the temperature at 50°C to 55°C, and start to add 45g of thionyl chloride dropwise. During the dropwise addition, dibromoneopentyl glycol gradually dissolves, and hydrogen chloride gas is generated, and the hydrogen chloride gas is absorbed with water. After the dropwise addition, the temperature was controlled at 50° C. to 55° C., and the temperature was kept for 2.0 hours. During the heat preservation process, samples were taken and analyzed by TLC. After the raw materials were completely reacted, the temperature was controlled below 70°C, and the solvent was recovered under reduced pressure until evaporated to dryness. After evaporating to dryness, 10 g of formamide was added to the residue to obtain 75 g of esterified product II / formamide mixture. Wherein the developer used for TLC detection is a mixed developer of petr...

Embodiment 3

[0047] Put 150ml of n-hexane into the reaction bottle, then add 50g of dibromoneopentyl glycol, stir and heat up to 30°C, during the dropwise addition, keep the temperature at 30°C-45°C, and start to add 30g of thionyl chloride dropwise. During the dropwise addition, dibromoneopentyl glycol gradually dissolves and hydrogen chloride gas is generated, and the generated hydrogen chloride gas is absorbed with water. After the dropwise addition, the temperature was controlled at 40° C. to 45° C. and kept for 4.0 hours. During the heat preservation process, samples were taken and analyzed by TLC. After the raw materials were completely reacted, the temperature was controlled below 70°C, and the solvent was recovered under reduced pressure until evaporated to dryness. After evaporating to dryness, 10 g (about 10 ml) of DMF was added to the residue to obtain esterified compound II / DMF mixture 75.

[0048] Put 150ml of DMF and 13g of zinc powder into another reaction bottle, stir, hea...

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Abstract

The invention provides an industrial production method for cyclopropyl sulfinate, belonging to the technical field of drug synthesis. The industrial production method comprises the following steps of: a. esterification reaction: carrying out esterification reaction on dibromo neopentyl glycol I used as a raw material and thionyl chloride to obtain an esterified product; b. cyclization reaction: adding zinc powder to an amide solution and dropwise adding the esterified product obtained in the step a for cyclization reaction; and c. complex reaction: adding a complexing agent for complex reaction to obtain cyclopropyl sulfinate. The industrial production method for cyclopropyl sulfinate provided by the invention has the advantages of use of one-pot reaction, simple process, low pollution and high yield and quality of a final product, is convenient to operate and is beneficial to industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing a drug intermediate, in particular to a method for industrially producing cyclopropyl sulfinate, an intermediate of montelukast sodium, and belongs to the technical field of drug synthesis. Background technique [0002] Montelukast sodium is an orally active leukotriene receptor antagonist, which can selectively combine with leukotriene in the airway, block the action of allergic mediators, improve respiratory inflammation, and unblock the airway. , low toxicity, good safety anti-asthma anti-inflammatory and anti-allergic drugs. Montelukast sodium has the effect of low-dose corticosteroids, and the side effects are lower than these substances. The structural formula of montelukast sodium is as follows: [0003] [0004] Cyclopropyl sulfinate is an important intermediate in the synthesis of montelukast sodium, a drug for the treatment of asthma. Cyclopropyl sulfinate is also known as 1,1-cyclopropa...

Claims

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Application Information

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IPC IPC(8): C07D327/10
Inventor 徐斌程锦涛陈斌
Owner 江苏八巨药业有限公司
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