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A kind of preparation method of l-alpha-glycerophosphocholine

A technology of glycerophosphocholine and glycerophosphate, which is applied in organic chemical methods, chemical instruments and methods, phosphorus organic compounds, etc., can solve pollution and other problems, and achieve the effects of reducing production costs, good application prospects, and high product purity

Active Publication Date: 2020-04-21
SHANGHAI KEYI BIOLOGICAL MEDICINE CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0027] The technical problem to be solved by this invention is to provide a kind of preparation method of L-α-glycerophosphorylcholine, which avoids the problem of a large amount of waste water pollution caused by the use of phosphorylcholine chloride calcium salt or potassium salt and the final product must be processed Ion exchange resin column removes chloride ions, the product has good purity and high yield, is suitable for industrial production, and has good application prospects

Method used

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  • A kind of preparation method of l-alpha-glycerophosphocholine
  • A kind of preparation method of l-alpha-glycerophosphocholine
  • A kind of preparation method of l-alpha-glycerophosphocholine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of (R)-glycerophosphate

[0043]

[0044] Take 212.3 g (1 mol) of potassium phosphate and 1000 ml of purified water, stir to dissolve, heat to 45-50°C, and add 110 g (1.0 mol) of (R)-3-chloro-1,2-propanediol dropwise. After dropping, keep warm for 2-3 hours. Cool to room temperature, and adjust the pH value to 4-5 with dilute hydrochloric acid. The water was distilled off to dryness. Add 500 ml of ethanol and heat to reflux, then heat filter to remove inorganic salts. Ethanol was distilled to dryness to obtain 149.53 g of the product, with a yield of 87.43%.

Embodiment 2

[0046] Preparation of (R)-glycerophosphate

[0047]

[0048]Take 164 g (1 mol) of sodium phosphate and 1000 ml of purified water, stir to dissolve, heat to 45-50°C, and add 100 g (0.9 mol) of (R)-3-chloro-1,2-propanediol dropwise. After dropping, keep warm for 2-3 hours. Cool to room temperature, and adjust the pH value to 4-5 with dilute hydrochloric acid. The water was distilled off to dryness. Add 500 ml of ethanol and heat to reflux, then heat filter to remove inorganic salts. Ethanol was distilled to dryness to obtain 130.86 g of the product, with a yield of 83.23%.

Embodiment 3

[0050] Preparation of (R)-3-Glyceryl Cycloethyl Phosphate

[0051]

[0052] Take 172 grams (1.0 moles) of (R)-glycerophosphate of Example 1, 1500 milliliters of absolute ethanol, stir and dissolve at room temperature, add 276.5 grams (2.0 moles) of anhydrous potassium carbonate, benzyltriethylammonium bromide 5 grams (0.02 moles; act as a phase transfer catalyst), 188 grams (1.0 moles) of dibromoethane, heated to reflux for 6 hours, then added 94 grams of dibromoethane (0.5 moles), and continued to reflux for 3 hours . Cool to room temperature and filter. The solvent was distilled to dryness. Add 500 ml of water and extract with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The solvent was distilled to dryness to obtain 130.02 g of a white solid product with a yield of 66.17%.

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Abstract

The invention relates to a preparation method of L-alpha-glycerophosphoryl choline. The method comprises the steps of preparing (R)-3-chlorine-1,2-propylene glycol as an initial raw material; preparing (R)-glycerophosphate with calcium phosphate metal salt; then carrying out a reaction with dibromoethane to obtain (R)-3-glyceryl cyclophosphate; finally carrying out a reaction with trimethylamine in an open-loop reaction to obtain L-alpha-glycerophosphoryl choline. With the adoption of the method, the problem of wastewater pollution caused by choline chloride phosphate calcium salt or potassiumsalt is avoided, and the link of removing chloridion of a finished product through ion-exchange columns can be eliminated; the product purity is high; the yield is high; the method is applicable to industrial production and has a good application prospect.

Description

technical field [0001] The invention belongs to the field of preparation of chiral drugs, in particular to a preparation method of L-alpha-glycerophosphocholine. Background technique [0002] L-α-Glycerophosphoryl Choline (L-α-GPC for short) is a naturally occurring water-soluble phospholipid metabolite in the body and a choline source for the synthesis of acetylcholine and phosphatidylcholine. Health function and medical application value. L-α-GPC can improve the cognitive ability of the brain, and even repair the partially damaged cognitive ability of patients with early senile dementia, and can protect liver tissue from toxic carbon tetrachloride and high-fat protein foods. The produced fatty acid penetrates, has anti-hyperlipidemia, protects blood vessels, and can promote the growth of adolescents and improve memory ability, so it is widely used in medicine, health products and functional foods. The chemical structural formula of L-α-GPC is as follows: [0003] [...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/09C07B53/00
CPCC07B53/00C07B2200/07C07F9/091
Inventor 李舸刘婷李海林王世运张建现彭自祥张明明张爱强
Owner SHANGHAI KEYI BIOLOGICAL MEDICINE CO LTD
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