Method for splitting 6,8-dichlorocaprylate

A technology of dichlorooctanoic acid and a splitting agent, which is applied in the splitting field of 6,8-dichlorooctanoic acid, can solve the problems of high price of ephedrine, unsuitable for splitting agent, complicated operation, etc. The effect of splitting yield and reducing environmental pollution

Inactive Publication Date: 2010-11-10
SHANGHAI INST OF PHARMA IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] ①(+)-6,8-Dichlorooctanoic acid or the salt formed by (-)-6,8-Dichlorooctanoic acid and ephedrine requires six times of recrystallization to obtain the pure product, which is cumbersome to operate and the yield is very low;
[0008] ②The price of ephedrine is relatively expensive, so it is not suitable as a resolving agent

Method used

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  • Method for splitting 6,8-dichlorocaprylate
  • Method for splitting 6,8-dichlorocaprylate
  • Method for splitting 6,8-dichlorocaprylate

Examples

Experimental program
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Effect test

Embodiment 1

[0027] In five identical 50ml single-necked flasks, add 5g (23.5mmol) (±)-6,8-dichlorooctanoic acid and 20ml ethyl acetate respectively, shake well, and then add 18.8mmol of resolution reagent cinchor Nidine, quinine, dehydroabietylamine, L-aminopropanol, cinchonine, stirred in a water bath at 40°C until clear. Slowly cool to 0 DEG C then, observe phenomenon and find, only add the resolving agent dehydroabietylamine in the flask that precipitates crystal, add in the flask that adds other resolving reagent or clarification does not have phenomenon, or separates out oily thing.

Embodiment 2

[0029] In a 50ml single-necked flask, add 2g (9.4mmol) (±)-6,8-dichlorooctanoic acid and 8ml ethyl acetate, shake well, then add 1.9g (6.6mmol) dehydroabietylamine, and Stir in a water bath until clear. Then it was slowly cooled to 0°C, and crystals were formed. After suction filtration, the collected crystals were recrystallized three times in ethyl acetate, and dried in vacuo to obtain 1.1 g of a white solid, which was a salt of (+)-6,8-dichlorooctanoic acid and dehydroabietylamine. Rotation, [α] 20 D: -11.2° (C=1, ethanol).

Embodiment 3

[0031] In a 100ml single-necked flask, add 8.8g (41.3mmol) (±)-6,8-dichlorooctanoic acid and 36ml ethyl acetate, shake well, then add 9.4g (33.1mmol) dehydroabietylamine, at 40 ℃ Stir in a water bath until clear. Then it was slowly cooled to 0°C, and crystals were formed. Suction filtration, the collected crystals were recrystallized three times in ethyl acetate, and dried in vacuo to obtain 5.2 g of a white solid, which was a salt of (+)-6,8-dichlorooctanoic acid and dehydroabietylamine, [α] 20 D: -12° (C=1, ethanol). The above white solid was basified with NaOH first, and the separated alkali solution was acidified with dilute hydrochloric acid to free (+)-6,8-dichlorooctanoic acid, then extracted with dichloromethane, dried, and concentrated to obtain an oil (+)-6,8-dichlorooctanoic acid. )-6,8-dichlorooctanoic acid 2.2g. Rotation, [α] 20 D: +30.0° (c=2, toluene)

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Abstract

The invention provides a method for optically splitting (+ / -)-6,8-dichlorocaprylate. In the method, dehydroabietylamine with a structure expressed as the following figure is used as a splitting reagent, the dehydroabietylamine is reacted with racemized (+ / -)-6,8-dichlorocaprylate to form a pair of diastereoisomer salts, and optical splitting is performed according to different solubility of the diastereoisomer salts to obtain (+)-6,8-dichlorocaprylate. Compared with the conventional splitting method, the splitting reagent is cheap and easily obtained, and the product is purified without repeated recrystallization.

Description

technical field [0001] The present invention relates to the preparation method of an important intermediate of (R)-lipoic acid: (+)-6,8-dichlorooctanoic acid, in particular to the resolution of (±)-6,8-dichlorooctanoic acid to obtain its single enantiomer Method for isomer (+)-6,8-dichlorooctanoic acid. Background technique [0002] The structural formula of (+)-6,8-dichlorooctanoic acid is as follows: [0003] [0004] (+)-6,8-Dichlorooctanoic acid is an important intermediate in the synthesis of (R)-lipoic acid. (R)-Lipoic acid is a multipurpose natural product belonging to vitamins. It participates in sugar metabolism as a coenzyme and has strong antioxidant properties. Together with (R)-dihydrolipoic acid, it is known as the "universal antioxidant", which can be applied to diabetes and chronic complications of diabetes. It can also be used as an additive in health and beauty products. Its structural formula is as follows: [0005] [0006] D.S.Acker etc. have ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C53/19C07C51/42
Inventor 李明黄成军
Owner SHANGHAI INST OF PHARMA IND CO LTD
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