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Novel synthesis route of pranlukast intermediate 4-(4-phenylbutoxyl)benzoic acid

A technology of phenyl butoxy sulfonate and phenyl butoxy, which is applied in the field of new synthetic route of pranlukast intermediate 4-benzoic acid, can solve the problem of unexplained starting material 4-chloro-1- Problems such as the preparation method of butanol, and achieve the effects of low cost, easy availability of raw materials, and good product purity

Inactive Publication Date: 2015-03-11
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0026] The synthetic route reported in this literature does not specify the preparation method of the starting material 4-chloro-1-butanol, and requires 4-chloro-1-butanol to be freshly prepared

Method used

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  • Novel synthesis route of pranlukast intermediate 4-(4-phenylbutoxyl)benzoic acid
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  • Novel synthesis route of pranlukast intermediate 4-(4-phenylbutoxyl)benzoic acid

Examples

Experimental program
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Embodiment 1

[0043] a. Synthesis of 4-phenylbutoxysulfonate

[0044] Add magnesium powder (2.64 g, 0.11 mol), a small grain of iodine and partially dried tetrahydrofuran (total 15 mL, 0.5 mol) and β-bromophenylethane (a total of 18.5 g, 0.1 mol) mixed solution, the reaction was initiated at 25 oC. After the reaction is initiated, slowly add the remaining tetrahydrofuran and β-bromophenylethane mixture dropwise under stirring, and control the dropping rate to keep the system slightly boiling. After the dropwise addition, continue heating to reflux for 0.5 h, stop heating, and cool to room temperature. The reaction system was placed in an ice-salt bath, and the temperature was kept at 0 oC. Ethylene oxide (4.4 g, 0.1 mol) was introduced into the reaction solution via catheter. After the feeding was completed, the ice bath was removed, and slowly heated to reflux in a water bath for 1 h, then cooled to room temperature, and the solvent tetrahydrofuran was distilled off to obtain a viscous ...

Embodiment 2

[0051] a. Synthesis of 4-phenylbutoxysulfonate

[0052] Add magnesium powder (2.64 g, 0.11 mol), a small grain of iodine and partially dried tetrahydrofuran (total 15 mL, 0.5 mol) and β-bromophenylethane (a total of 18.5 g, 0.1 mol) mixed solution, the reaction was initiated at 25 oC. After the reaction is initiated, slowly add the remaining tetrahydrofuran and β-bromophenylethane mixture dropwise under stirring, and control the dropping rate to keep the system slightly boiling. After the dropwise addition, continue heating to reflux for 0.5 h, then stop heating, and then lower to room temperature. The reaction system was placed in an ice-salt bath, the temperature was maintained at 3 oC, and ethylene oxide (4.4 g, 0.1 mol) was introduced into the reaction solution through a catheter. After the feeding was completed, the ice bath was removed, and slowly heated to reflux in a water bath for 1 h, then cooled to room temperature, and the solvent tetrahydrofuran was distilled of...

Embodiment 3

[0059] a. Synthesis of 4-phenylbutoxysulfonate

[0060] Add magnesium powder (2.64 g, 0.11 mol), a small grain of iodine and partially dried tetrahydrofuran (total 15 mL, 0.5 mol) and β-bromophenylethane (a total of 18.5 g, 0.1 mol) mixed solution, the reaction was initiated at 25 oC. After the reaction is initiated, slowly add the remaining tetrahydrofuran and β-bromophenylethane mixture dropwise under stirring, and control the dropping rate to keep the system slightly boiling. After the dropwise addition, continue heating to reflux for 0.5 h, then stop heating, and then lower to room temperature. The reaction system was placed in an ice-salt bath at a temperature of 5 oC. Ethylene oxide (4.84 g, 0.11 mol) was introduced into the reaction solution through a catheter. After the feeding was completed, remove the ice bath, slowly heat and reflux in a water bath for 1 h, then cool to room temperature, distill off the solvent tetrahydrofuran, and the reaction system is viscous ...

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Abstract

The invention discloses a novel synthesis route of a pranlukast intermediate 4-(4-phenylbutoxyl)benzoic acid, and belongs to the field of pharmaceutical chemistry. The novel synthesis route is characterized in that: cheap beta-bromophenylethane is taken as the primary raw material, and then the primary raw material is subjected to Grignard reaction, p-epoxy ethane addition reaction, mesylation, substitution reaction, and hydrolysis so as to obtain 4-(4-phenylbutoxyl)benzoic acid. The provided novel synthesis route has the characteristics of cheap and available raw materials, short technology route, high product purity, high yield, and low cost, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the synthesis of medicines, in particular to a new synthesis route of pranlukast intermediate 4-(4-phenylbutoxy)benzoic acid. Background technique [0002] As an anti-asthma drug, Pranlukast was first successfully developed by Japan Ono Company, and it was launched in Japan in 1995. In 1999, it was found to be able to treat allergic rhinitis. [0003] Prankast is a leukotriene C4 / D4 receptor antagonist (lTRAs) with extremely low toxicity. It can selectively inhibit the activity of airway smooth muscle leukotriene polypeptides and has little effect on arachidonic acid metabolic enzymes , At the same time, it has no antagonistic effect on acetylcholine and 5-hydroxytryptamine, but has significant inhibition on lTC4, lTD4, lTE4, etc. Studies have shown that in clinical application, pranlukast not only has a good therapeutic effect on atopic asthma, but also on other types of bronchial asthma such as mixed type, infectious type, p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C65/24C07C51/02
CPCC07C51/02C07C51/09C07C67/31C07C303/26C07C65/24C07C69/94C07C309/66
Inventor 郑庚修马小芬王秋芬赵承彪杨柳付凯
Owner UNIV OF JINAN
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