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Gemfibrozil composite method

A synthetic method and the technology of gemfibrozil, which are applied in the field of preparation of the compound gemfibrozil, can solve problems such as harsh reaction conditions, expensive n-butyllithium, and dangerous operation, and achieve simple operation, cost reduction, and environmental protection. pollution effect

Inactive Publication Date: 2010-06-09
SHANGHAI INST OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

n-Butyllithium is expensive, dangerous to operate, and harsh reaction conditions

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] In a 250mL three-necked flask, add 2,5-xylenol (15.3g, 0.125moL), tetrabutylammonium bromide (0.8g, 0.0025moL), tert-butyl 5-bromo-2,2-dimethylpentanoate Ester (37.1g, 0.14moL), sodium hydroxide (7.2g, 0.18moL) and water 40mL. After the mixture was heated to 95° C. for 10 hours, sodium hydroxide (12 g, 0.3 moL) was added to continue the reaction for 9 hours. After the reaction was complete, 200 mL of water was added and cooled to room temperature. Add concentrated hydrochloric acid to adjust pH=1~2, stir and filter to obtain a yellow solid. The solid was recrystallized from aqueous methanol to obtain 30.0 g of the product, with a yield of 90.5%, an HPLC content of 99.3%, and a melting point of 60-62°C (literature value of 61-63°C).

Embodiment 2

[0043] In a 250mL three-necked flask, add 2,5-xylenol (15.3g, 0.125moL), tetrabutylammonium bromide (0.8g, 0.0025moL), 5-chloro-2,2-dimethylpentanoic acid isopropyl Ester (30.9g, 0.15moL), sodium hydroxide (7.2g, 0.18moL) and water 40mL. After the mixture was heated to 95° C. for 10 hours, sodium hydroxide (12 g, 0.3 moL) was added to continue the reaction for 10 hours. After the reaction was complete, 200 mL of water was added and cooled to room temperature. Add concentrated hydrochloric acid to adjust pH=9~10, stir, filter, dissolve the filter cake in water, acidify with concentrated hydrochloric acid, filter, and distill the filter cake under reduced pressure to obtain product 29.3, yield 88.4%, HPLC content 99.1%, melting point 60-62 ℃.

Embodiment 3

[0045] In a 250mL three-necked flask, add 2,5-xylenol (15.3g, 0.125moL), PEG6000 (0.0025moL), 5-bromo-2,2-dimethylpentanoic acid isobutyl ester (37.1g, 0.14moL) , potassium carbonate (42.4g, 0.4moL) and water 60mL. After the mixture was heated to 100° C. for 18 hours, potassium hydroxide (16.5 g, 0.28 moL) was added to continue the reaction for 8 hours. After the reaction was complete, 200 mL of water was added and cooled to room temperature. Add concentrated hydrochloric acid to adjust pH=9~10, stir, filter, dissolve the filter cake in water, acidify with concentrated hydrochloric acid, filter, and distill the filter cake under reduced pressure to obtain product 28.3, yield 85.3%, HPLC content 99.2%, melting point 60-62 ℃.

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Abstract

The invention discloses a Gemfibrozil composite method. 2, 5-dimethyl phenol and 5-halogenate-2,2-dimethyl valerate are subjected to condensation polymerization in the presence of alkali under the action of phase transfer catalyst; alkali is added for hydrolysis reaction to obtain the product of Gemfibrozil. The invention simultaneously carries out condensation and hydrolysis in the same kettle and has simple operation; in the technical process, no organic solvent is added, so that the invention has small pollution to environment and low cost.

Description

technical field [0001] The invention relates to a preparation method of compound gemfibrozil. technical background [0002] Gemfibrozil (Gemfibrozil, formula III), chemical name 2,2-dimethyl-5-(2,5-dimethylphenoxy)valeric acid, belongs to clofibrate derivatives blood lipid regulating drugs, It was developed and listed by the United States in 1982. The drug can be used to prevent arteriosclerosis, and help reduce the incidence of myocardial infarction, with less toxic side effects. [0003] [0004] The synthetic method of bibliography gemfibrozil mainly contains following several kinds: [0005] ES549470 uses 3-(2,5-dimethylphenoxy)-1-bromopropane 1 as raw material to make Grignard reagent and reacts with acetone to obtain 2-methyl-5-(2,5-dimethylbenzene Oxy)-propanol 2, then with SOCl 2 The product halocarbon 3 obtained by the action is then made into a Grignard reagent and then reacted with CO 2 The reaction gives the product gemfibrozil (Scheme 1). Grignard react...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/13C07C51/09B01J31/02
Inventor 吴范宏杨雪艳俞晓东
Owner SHANGHAI INST OF TECH
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