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Environment-friendly preparation method for lipid-lowering drug ciprofibrate

A green and pharmaceutical technology, applied to the preparation of organic compounds, carboxylate preparation, chemical instruments and methods, etc., can solve the problems of long reaction route and complicated reaction steps, and achieve high reaction yield, few steps, and easy operation simple effect

Active Publication Date: 2013-10-30
SHANGHAI TIANCI BIOLOGICAL VALLEY BIOLOGICAL ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Although this method satisfies the conditions of environmental friendliness, the reaction steps are complicated and the reaction route is long.

Method used

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  • Environment-friendly preparation method for lipid-lowering drug ciprofibrate
  • Environment-friendly preparation method for lipid-lowering drug ciprofibrate
  • Environment-friendly preparation method for lipid-lowering drug ciprofibrate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) Preparation of 2-methyl-2-(4-vinylphenoxy)propionic acid

[0031] Add 1kg of p-hydroxystyrene, 3L of acetone, and 1kg of sodium hydroxide into a 10L flask, stir for 30 minutes, then add 1.5kg of chloroform dropwise, stir for 30 minutes after the dropwise addition, and raise the temperature to 70°C. After the reaction is complete, evaporate the solvent to dryness, and add 4000ml Water and 3000ml of dichloromethane, decolorized the water layer with activated carbon, adjusted the pH to 2-3 with 2mol / L hydrochloric acid, precipitated a white product, collected the solid by filtration to obtain 2-methyl-2-(4-vinylphenoxy ) Propionic acid 1.6kg, molar yield 93%. 1 H-NMR (500MHz, CDCl 3 ) δ: 1.65(s,6H), 5.22(d,1H), 5.67(d,1H), 6.69(m,1H), 6.92(d,2H), 7.35(d,2H).

[0032] (2) Preparation of ciprofibrate

[0033] Dissolve 653g of 2-methyl-2-(4-vinylphenoxy)propionic acid in 900ml of chloroform, add 500ml of water, 160g of NaOH, 11g of tetrabutylammonium bromide, stir at r...

Embodiment 2

[0035] (1) Preparation of 2-methyl-2-(4-vinylphenoxy)propionic acid

[0036] Add 1kg of p-hydroxystyrene, 5L of acetone, and 1.8kg of potassium hydroxide into a 10L flask, stir for 30 minutes, then add 2.0kg of chloroform dropwise, stir for 30 minutes after the dropwise addition, control the temperature at 30-40°C, evaporate to dryness after the reaction is complete Solvent, add 5000ml of water and 3000ml of dichloromethane, decolorize the water layer with activated carbon, adjust the pH to 2-3 with 3mol / L hydrochloric acid, precipitate a white product, collect the solid by filtration to obtain 2-methyl-2-(4-ethylene 1.63kg of propionic acid, the molar yield is 94.5%. 1 H-NMR (500MHz, CDCl 3 ) δ: 1.65(s,6H), 5.22(d,1H), 5.67(d,1H), 6.69(m,1H), 6.92(d,2H), 7.35(d,2H).

[0037] (2) Preparation of ciprofibrate

[0038] Dissolve 653g of 2-methyl-2-(4-vinylphenoxy)propionic acid in 1000ml of chloroform, add 500ml of water, 280g of potassium hydroxide, 20g of benzyltriethylammoni...

Embodiment 3

[0040] (1) Preparation of 2-methyl-2-(4-vinylphenoxy)propionic acid

[0041] Add 1kg of p-hydroxystyrene and 5L of acetone to a 10L flask, control the temperature at 0°C, add 3kg of potassium tert-butoxide in batches, stir for 30 minutes, then add 2.0kg of chloroform dropwise at a temperature of 0-10°C, and stir for 30 minutes after the addition , control the temperature at 30-40°C, after the reaction is complete, evaporate the solvent to dryness, add 5000ml of ice water, then add 3000ml of dichloromethane, decolorize the water layer with activated carbon, adjust the pH to 2-3 with 3mol / L hydrochloric acid, and precipitate The white product was collected by filtration to obtain 1.63 kg of 2-methyl-2-(4-vinylphenoxy)propionic acid, with a molar yield of 94.5%. 1 H-NMR (500MHz, CDCl 3 ) δ: 1.65(s,6H), 5.22(d,1H), 5.67(d,1H), 6.69(m,1H), 6.92(d,2H), 7.35(d,2H).

[0042] (2) Preparation of ciprofibrate

[0043]Dissolve 653g of 2-methyl-2-(4-vinylphenoxy)propionic acid in 1000ml...

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PUM

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Abstract

The invention provides an environment-friendly preparation method for a lipid-lowering drug ciprofibrate. The preparation method comprises the following steps of by taking hydroxyphenyl ethene as a raw material, carrying out Bargellini and annulation reaction to prepare the ciprofibrate. Compared with the traditional method, the method has the advantages of less reaction steps, short production cycle and high total yield, is easy to operate, mild and easy-control in conditions, convenient for postprocessing and environment-friendly, and is a brand new method for industrialized synthesis of the ciprofibrate.

Description

technical field [0001] The invention relates to the preparation of blood lipid-lowering drugs, in particular to a green preparation method of ciprofibrate. Background technique [0002] Ciprofibrate, also known as clofibrate, is a phenoxyacetic acid hypolipidemic drug, which is stronger than clofibrate, can significantly reduce the level of very low density lipoprotein and low density lipoprotein, and increase high Density lipoprotein levels also have the effect of dissolving fibrin and preventing platelet aggregation. The chemical name is 2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropionic acid, and its structural formula is as follows: [0003] [0004] (I) [0005] In CN1514819, it is disclosed that a compound 2,2-dichlorocyclopropylbenzene is used as a raw material, undergoes Friedel-Crafts acylation, and performs Baeyer-Villiger rearrangement with peroxyacids to obtain phenolic esters, after alcoholysis of phenolic esters Obtain phenolic compounds, and then r...

Claims

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Application Information

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IPC IPC(8): C07C51/347C07C59/72
Inventor 汪迅李新涓子李勇刚高艳吕兴红沈小良施乐乐
Owner SHANGHAI TIANCI BIOLOGICAL VALLEY BIOLOGICAL ENG
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