Preparation method of (R)-3-palmitoyl oxybutyric acid

A technology of palmitoyloxybutyric acid and tert-butyl palmitoyloxybutyrate, which is applied in the field of preparation of -3-palmitoyloxybutyric acid, can solve the problems of acidosis and difficult penetration of the blood-brain barrier, etc. Achieve the effects of simple route, easy industrial production, and simple process

Inactive Publication Date: 2021-07-09
NANJING NUTRABUILDING BIO TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, (R)-3-hydroxybutyric acid is a medium-strong acid, which is not easy to pass through the blood-brain barrier, and it will be absorbed rapidly in the gastrointestinal tract when taken directly, resulting in acidosis

Method used

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  • Preparation method of (R)-3-palmitoyl oxybutyric acid
  • Preparation method of (R)-3-palmitoyl oxybutyric acid
  • Preparation method of (R)-3-palmitoyl oxybutyric acid

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Embodiment 1

[0045] Embodiment 1: the preparation of (R)-3-palmitoyloxybutyric acid

[0046]

[0047] Add 200g of tert-butyl acetoacetate to the autoclave, add 200mL of methanol, and add 400mg of (R)-BINAP-Ru. Nitrogen replacement three times, hydrogen replacement three times. React under 3MPa at 35-45°C for 16 hours, and monitor the completion of the reaction. Methanol was distilled off under reduced pressure. The residue was distilled under reduced pressure to obtain 184 g of tert-butyl (R)-3-hydroxybutyrate as a colorless oil. Yield: 92%, chemical purity: 99%, optical purity: 99%.

[0048]100g (R)-tert-butyl 3-hydroxybutyrate was placed in a 2L flask, and 600mL of dichloromethane, 76g (1.2eq.) of triethylamine, and 1g of DMAP were added. 189g of hexadecanoyl chloride (1.1eq.) was added at 15-25°C. Keep warm for 10-16 hours, and monitor the completion of the reaction. The reaction solution was suction filtered, the filtrate was added with water, washed and separated, and the org...

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Abstract

The invention discloses a preparation method of (R)-3-palmitoyloxy butyric acid. The method comprises the following steps: by taking tert-butyl acetoacetate as an initial raw material, carrying out hydrogenation reaction under the catalysis of RuCl2 [(R)-BINAP]; then in the presence of alkali and under the action of a catalyst, carrying out acylation reaction with palmitoyl chloride; and finally, carrying out deprotection reaction in the presence of acid, and removing tert-butyl to obtain (R)-3-palmitoyloxy butyric acid. The route is simple, only three-step reaction is adopted, the total yield is greater than or equivalent to 70%, the chemical purity of the product is larger than or equal to 98%, and the chiral purity is larger than or equal to 99%; the process is simple, stable in quality and easy for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of (R)-3-palmitoyloxybutyric acid. Background technique [0002] (R)-3-Hydroxybutyric acid is an endogenous ketone body. On the one hand, it can participate in the tricarboxylic acid cycle as an intermediate, and on the other hand, it can provide alternative fuel for the brain, skeletal muscle, and cardiac muscle. It has been reported that (R)-3-hydroxybutyric acid can improve cognition or be used for the prevention and treatment of cardiovascular diseases, diabetes, epilepsy and nervous system diseases. However, (R)-3-hydroxybutyric acid is a medium-strong acid, which is difficult to pass through the blood-brain barrier, and if taken directly, it will be absorbed rapidly in the gastrointestinal tract and cause acidosis. On the one hand, (R)-3-palmitoyloxybutyric acid can easily pass through the blood-brain barrier; on the other hand, it can be s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/29C07C69/24
CPCC07C67/29C07C67/31
Inventor 朱赢张健廖琪林
Owner NANJING NUTRABUILDING BIO TECH CO LTD
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