Preparation method of lipoic acid process impurity

A technology for processing impurities and lipoic acid, applied in the direction of organic chemistry, etc., to achieve the effect of single product, high selectivity, and avoiding the formation of impurities

Inactive Publication Date: 2020-06-23
JIANGSU TOHOPE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on the preparation of 1,2,3-trithiocyclohexane-4-pentanoic acid (with the structure of formula I), the main process impurity of lipoic acid

Method used

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  • Preparation method of lipoic acid process impurity
  • Preparation method of lipoic acid process impurity
  • Preparation method of lipoic acid process impurity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Put 10.00g (41.5mmol) of ethyl 6,8-dichlorooctanoate, (100mL) water, and 1.83g (45.7mmol) of sodium hydroxide into a 500mL three-necked flask, stir, heat up to 65°C, and react After 3 hours, the reaction was completed, lowered to room temperature, and then slowly added dropwise a solution of 6.64g (207.5mmol) sulfur and 19.92g (83.0mmol) sodium sulfide nonahydrate in water (100mL) that had been prepared in advance. After the dropwise addition was completed, the temperature was raised React at 50°C for 6 hours. After the reaction is complete, cool down to room temperature. Adjust the pH of the system to 1-2 with 10% dilute phosphoric acid prepared in advance. A large amount of off-white solid precipitates. Keep stirring and crystallizing for 0.5 hours and then filter to collect the crude solid. , and then the solid crude product was placed in a 250 mL three-neck flask, recrystallized with an appropriate amount of ethanol and water, and finally 9.08 g of the target impurit...

Embodiment 2

[0026] Put 10.00g (41.5mmol) ethyl 6,8-dichlorooctanoate, (100mL) water, and 1.66g (41.5mmol) sodium hydroxide into a 500mL three-necked flask, stir, heat up to 65°C, and react After 3 hours, the reaction was completed, lowered to room temperature, and then slowly added dropwise a solution of 6.64g (207.5mmol) sulfur and 19.92g (83.0mmol) sodium sulfide nonahydrate in water (100mL) that had been prepared in advance. After the dropwise addition was completed, the temperature was raised React at 50°C for 6 hours. After the reaction is complete, cool down to room temperature. Adjust the pH of the system to 1-2 with 10% dilute phosphoric acid prepared in advance. A large amount of off-white solid precipitates. Keep stirring and crystallizing for 0.5 hours and then filter to collect the crude solid. , and then the solid crude product was placed in a 250 mL three-neck flask, recrystallized with an appropriate amount of ethanol and water, and finally 8.95 g of the target impurity was ...

Embodiment 3

[0028] Put 10.00g (41.5mmol) of ethyl 6,8-dichlorooctanoate, (100mL) water, and 1.74g (43.6mmol) of sodium hydroxide into a 500mL three-necked flask, stir, and raise the temperature to 65°C to react After 3 hours, the reaction was completed, lowered to room temperature, and then slowly added dropwise a solution of 6.64g (207.5mmol) sulfur and 14.95g (62.3mmol) sodium sulfide nonahydrate in water (100mL) that had been prepared in advance. After the dropwise addition was completed, the temperature was raised React at 50°C for 6 hours. After the reaction is complete, cool down to room temperature. Adjust the pH of the system to 1-2 with 10% dilute phosphoric acid prepared in advance. A large amount of off-white solid precipitates. Keep stirring and crystallizing for 0.5 hours and then filter to collect the crude solid. , and then the solid crude product was placed in a 250 mL three-neck flask, recrystallized with an appropriate amount of ethanol and water, and finally 9.26 g of th...

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Abstract

The invention relates to a preparation method of a lipoic acid process impurity namely 1,2,3-trithiocyclohexane-4-valeric acid, and belongs to the technical field of preparation of lipoic acid impurities. The preparation method comprises the following steps: carrying out saponification, vulcanization cyclization, acidification, and refining on a lipoic acid intermediate namely 6,8-dichloroethyl caprylate to obtain the product. The preparation method is simple in process, and high in operability and the product is easy to purify.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of lipoic acid process impurity 1,2,3-trithiocyclohexane-4-pentanoic acid. Background technique [0002] Alpha lipoic acid is a coenzyme found in mitochondria, similar to vitamins, which can eliminate free radicals that lead to accelerated aging and disease. Alpha lipoic acid enters the cells after being absorbed by the intestines in the body, and has both fat-soluble and water-soluble properties. Lipoic acid belongs to a class of compounds in the B vitamins. It is a growth factor for yeast and some microorganisms. It acts as a coenzyme in a multi-enzyme system and catalyzes the oxidative decarboxylation of pyruvate into acetic acid and the oxidative decarboxylation of α-ketoglutarate into succinic acid. It plays the role of transacyl in the reaction, and its chemical name is 5-[3-(1,2-dithioheterocycle)]pentanoic acid, which has the structure ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D341/00
CPCC07D341/00
Inventor 袁跃华陆惠刚龚利锋
Owner JIANGSU TOHOPE PHARMA
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