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Novel process for synthesizing Pranlukast intermediate p-phenylbutoxybenzoic acid

A technology of phenbutoxybenzoic acid and methyl phenbutoxybenzoate, applied in the field of pharmaceutical synthesis, can solve the problems such as the preparation method of starting material 4-chloro-1-butanol is not described, and achieves low cost, The effect of safe reaction and easy availability of raw materials

Inactive Publication Date: 2015-03-04
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0025] The synthetic route reported in this document 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 process for synthesizing Pranlukast intermediate p-phenylbutoxybenzoic acid
  • Novel process for synthesizing Pranlukast intermediate p-phenylbutoxybenzoic acid
  • Novel process for synthesizing Pranlukast intermediate p-phenylbutoxybenzoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] a. Synthesis of 4-phenylchlorobutane

[0042] In a 100 mL three-necked flask, add dry 1,4-dichlorobutane (15 mL) and dry benzene (5 mL), stir in an ice bath at 4~5 oC, add aluminum trichloride (2.26 g). After the reaction, slowly add 10 mL of ice water and concentrated hydrochloric acid mixture (volume ratio: 5:1), stir for 10 min, separate the organic phase, extract the water phase with benzene, combine the organic phases, and wash twice with 20 mL of water , the resulting organic phase was treated with MgSO 4 Dry, filter, and remove unreacted benzene and 1,4-dichlorobutane from the filtrate under reduced pressure, and the obtained light yellow transparent liquid is 4-phenylchlorobutane.

[0043] b. Synthesis of methyl p-phenylbutoxybenzoate

[0044] In a 100 mL three-necked flask, add the above product 4-phenylchlorobutane, DMF (15 mL). Under mechanical stirring, sequentially add methyl p-hydroxybenzoate (0.6 g, 3.95 mmol), potassium carbonate (1.1 g, 7.9 mmol), N...

Embodiment 2

[0048] a. Synthesis of 4-phenylchlorobutane

[0049] In a 100 mL three-neck flask, add dry 1,4-dichlorobutane (20 mL) and dry benzene (5 mL), stir in an ice bath at 4-5 oC, and add aluminum trichloride (2.9 g) in batches . After the reaction, slowly add 10 mL of ice water and concentrated hydrochloric acid mixture (volume ratio: 5:1), stir for 10 min, separate the organic phase, extract the water phase with benzene, combine the organic phases, wash twice with 20 mL of water, The obtained organic phase was treated with MgSO 4 Dry, filter, and remove unreacted benzene and 1,4-dichlorobutane from the filtrate under reduced pressure, and the obtained light yellow transparent liquid is 4-phenylchlorobutane.

[0050] b. Synthesis of methyl p-phenylbutoxybenzoate

[0051] In a 100 mL three-necked flask, add the above product 4-phenylchlorobutane, DMF (15 mL). Under mechanical stirring, sequentially add methyl p-hydroxybenzoate (0.6 g, 3.95 mmol), potassium carbonate (1.1 g, 7.9 mmo...

Embodiment 3

[0055] a. Synthesis of 4-phenylchlorobutane

[0056] In a 100 mL three-necked flask, add 25 mL of dry 1,4-dichlorobutane and 5 mL of dry benzene, stir in an ice bath at 10 °C, and add aluminum trichloride (3.76 g) in batches. After the reaction, slowly add 10 mL of ice water and concentrated hydrochloric acid mixture (volume ratio: 5:1), stir for 10 min, separate the organic phase, extract the water phase with benzene, combine the organic phases, wash twice with 20 mL of water, The obtained organic phase was treated with MgSO 4 Dry, filter, and remove unreacted benzene and 1,4-dichlorobutane from the filtrate under reduced pressure, and the obtained light yellow transparent liquid is 4-phenylchlorobutane.

[0057] b. Synthesis of methyl p-phenylbutoxybenzoate

[0058] In a 100 mL three-necked flask, add the above product 4-phenylchlorobutane, DMF (15 mL). Under mechanical stirring, sequentially add methyl p-hydroxybenzoate (0.6 g, 3.95 mmol), potassium carbonate (1.1 g, 7.9...

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PUM

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Abstract

The invention discloses a novel process for synthesizing Pranlukast intermediate p-phenylbutoxybenzoic acid, belonging to the field of medicinal chemistry. The process is characterized by comprising the following steps: by using low-price 1,4-dichlorobutane as an initial raw material, carrying out reactions such as Friedel-Crafts alkylation, substitution and hydrolysis, thereby obtaining the p-phenylbutoxybenzoic acid. The method has the characteristics of cheap and easily available raw materials, short process route, low cost, reaction safety, environment friendliness and the like and is suitable for industrial production.

Description

technical field [0001] The invention relates to drug synthesis, in particular to a new process for synthesizing pranlukast intermediate p-phenylbutoxybenzoic acid. Background technique [0002] In June 1995, the anti-asthma drug Pranlukast was launched in Japan, and since November 1999, it has been used to treat allergic rhinitis at the same time. 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, 5-HT, etc., and has significant inhibitory effects on LTC4, LTD4, LTE4, etc., especially on LTD4 (the main component that causes the contraction of human tracheal smooth muscle). It has an inhibitory effect on the occurrence and development of asthma And control plays an important role, it does not affect the P450 drug enzyme, there...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C65/24C07C51/09C07C27/02
CPCC07C51/09C07C17/32C07C67/31
Inventor 郑庚修马小芬王秋芬赵攀峰杨柳宋倩陈环宇
Owner UNIV OF JINAN
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