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Preparation method of R-lipoic acid tromethamine salt

A technology of lipoic acid tromethamine and lipoic acid is applied in the field of preparation of R-lipoic acid tromethamine, can solve the problems of high cost, environmental pollution, multiple crystallization and the like, and meets the requirements of industrial scaled production , good green environmental protection effect, the effect of reducing process steps

Inactive Publication Date: 2016-06-01
SUZHOU FUSHILAI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation of the aforementioned R-lipoic acid has a complex process, requires multiple crystallizations, high cost, and low yield, and because (S)-lipoic acid cannot be effectively utilized, it not only causes waste of resources, but also pollutes the environment

Method used

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  • Preparation method of R-lipoic acid tromethamine salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] A) Preparation of R-lipoic acid: first put (S)-6,8-dichlorooctanoic acid ethyl ester and sulfur prepared by biological enzyme into the reaction vessel equipped with a stirring device, raise the temperature to 70°C, and drop the mass The sodium sulfide aqueous solution with a percentage concentration of 8% carries out the cyclization reaction, and the cyclization reaction time is 5 hours, and the molar ratio of (S)-6,8-dichlorooctanoic acid ethyl ester, sulfur and sodium sulfide aqueous solution is 1:1.7:1 , kept at a temperature of 70°C for 2 hours, the cyclization reaction was completed, extracted with the first organic solvent, that is, toluene, and concentrated to obtain a cyclization solution, and then put the cyclization solution into a reaction vessel equipped with a stirring device and added mass percent The concentration is 4% sodium hydroxide solution for hydrolysis reaction, the molar ratio of the cyclization solution and the mass percentage concentration of 4%...

Embodiment 2

[0026]A) Preparation of R-lipoic acid: first put (S)-6,8-dichlorooctanoic acid ethyl ester and sulfur prepared by biological enzyme into a reaction vessel equipped with a stirring device, raise the temperature to 80°C, and add mass The sodium sulfide aqueous solution with a percentage concentration of 20% carries out the cyclization reaction, the cyclization reaction time is 0.5 hours, and the molar ratio of (S)-6,8-dichlorooctanoic acid ethyl ester, sulfur and sodium sulfide aqueous solution is 1:1.5:1 , kept at a temperature of 80°C for 1.5h, the cyclization reaction was completed, and the first organic solvent was extracted with ethyl acetate, concentrated to obtain a cyclization solution, and then the cyclization solution was put into a reaction vessel equipped with a stirring device and Adding the potassium hydroxide solution that the mass percentage concentration is 3% carries out hydrolysis reaction, and the mol ratio of the cyclization liquid and the mass percentage con...

Embodiment 3

[0029] A) Preparation of R-lipoic acid: First, put (S)-6,8-dichlorooctanoic acid ethyl ester and sulfur prepared by biological enzyme into the reaction vessel equipped with a stirring device, raise the temperature to 90°C, and drop the mass The sodium sulfide aqueous solution with a percentage concentration of 12% carries out the cyclization reaction, the cyclization reaction time is 3 hours, and the molar ratio of (S)-6,8-dichlorooctanoic acid ethyl ester, sulfur and sodium sulfide aqueous solution is 1:2:1.5 , kept at a temperature of 90°C for 1 hour, the cyclization reaction was completed, and the first organic solvent was used for extraction with cyclohexane, concentrated to obtain a cyclization solution, and then the cyclization solution was put into a reaction vessel equipped with a stirring device and added The sodium carbonate solution with a mass percentage concentration of 8% is hydrolyzed, the molar ratio of the cyclization liquid and the sodium carbonate solution wi...

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Abstract

The invention discloses a preparation method of R-lipoic acid tromethamine salt and belongs to the field of organic medicinal chemistry. The method includes the steps that (S)-6,8-dichloro ethyl caprylate and sulphur are put into a reaction vessel, the temperature is raised, a cyclization reaction is carried out, the temperature is preserved, extraction is carried out with a first organic solvent, concentration is carried out, and cyclization liquid is obtained; then, a hydrolysis reaction is carried out, cooling is carried out, and hydrolysis liquid is obtained; a second organic solvent is added into the hydrolysis liquid, the pH value is regulated, extraction is carried out, an obtained organic layer is washed with water to be neutral, the second organic solvent is removed at reduced pressure, and an initial product is obtained; mixed liquor is added into the initial product, the temperature is raised, a first filter aid is added, stirring adsorption is carried out, filtration is carried out, and light yellow liquid is obtained; cooling is carried out to separate out crystals, and R-lipoic acid is obtained; R-lipoic acid is dissolved, trihydroxymethyl aminomethane is added, the temperature is raised for solution, a second filter aid is added for filtration, and light yellow liquid is obtained; cooling is carried out to separate out crystals, centrifugal drying is carried out, and the finished product is obtained. According to the method, few steps are needed, efficiency is high, energy is saved, and waste discharge is reduced.

Description

technical field [0001] The invention belongs to the field of organic medicinal chemistry, and in particular relates to a preparation method of R-lipoic acid tromethamine salt. Background technique [0002] R-lipoic acid tromethamine salt (R(α) Alphalipoic Acid Tromethaminesalt) is a derivative of R-lipoic acid, its molecular weight is 327.46, and its chemical structural formula is as follows: [0003] [0004] Since R-lipoic acid tromethamine salt has anti-inflammatory and cell-protective activity (EP427247), it is used for the treatment of diabetes and insulin resistance (DE4,343,593), for the metabolic disorder of glucose in the central nervous system (ZNS) (DE4 , 343,592) and as an appetite suppressant (DE 19,818,563), thus having good medical uses eg in medicinal preparations (EP702953). [0005] Studies have shown that: R-lipoic acid tromethamine salt has potential therapeutic value for treating acidosis; insulin-dependent and glucose metabolism disordered diabetes;...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D339/04
CPCC07D339/04
Inventor 丁建飞
Owner SUZHOU FUSHILAI PHARMA CO LTD
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