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L-alpha-choline glycerophosphate synthesis method

A technology of glycerophosphocholine and a synthetic method, applied in the field of chiral synthetic chemistry and medicinal chemistry, can solve the problems of trivial details, unstable purification of glycerol, high cost of D-isopropylidene glycerol, etc., and achieves concise steps and high yield High, easily obtainable results

Inactive Publication Date: 2013-05-08
SHANGHAI CHENPON PHARM TECH CO LTD
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0019] The purpose of this invention is to provide a kind of new synthetic method of L-alpha-glycerophosphorylcholine, to overcome the weak point that existing synthetic method exists, especially the high cost of D-isopropylidene glycerol and (R) -(+)-Condensed Glycerol Instability Defect and Its Purification Complicated

Method used

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  • L-alpha-choline glycerophosphate synthesis method
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  • L-alpha-choline glycerophosphate synthesis method

Examples

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Embodiment 1

[0032] Embodiment 1, the preparation of phosphorylcholine tetramethylammonium salt

[0033] 100g (0.3mol) phosphorylcholine chloride calcium salt tetrahydrate was dissolved in 350mL water, heated to 50°C, 27g (0.3mol) oxalic acid was added thereto, stirred and reacted, and the calcium ion was completely precipitated, filtered with suction to obtain The filtrate was concentrated to dryness under reduced pressure under heating to obtain an oily substance, which was phosphorylcholine chloride. Add 300mL methanol to it, stir evenly, then add 54g (0.3mol) tetramethylammonium hydroxide pentahydrate, stir until completely dissolved, then remove the solvent under vacuum at 50°C to obtain 87.7g phosphorylcholine tetramethylammonium salt .

Embodiment 2

[0034] Embodiment two, the preparation of L-alpha-glycerophosphorylcholine crude product

[0035] Dissolve 87.7g (0.3mol) phosphorylcholine tetramethylammonium salt in 300mL water, add 33g (0.3mol) (R)-(-)-3-chloro-1,2-propanediol, heat to reflux overnight, cool, The water was distilled off under reduced pressure, 300 mL of ethanol was added to the residue, the slurry was beaten, the ammonium salt was removed by filtration, and the ethanol was distilled off the filtrate under reduced pressure to obtain about 70 g of crude L-α-glycerophosphorylcholine.

Embodiment 3

[0036] Embodiment three, the preparation of L-alpha-glycerophosphorylcholine crude product

[0037] Dissolve 87.7g (0.3mol) phosphorylcholine tetramethylammonium salt in 300mL methanol, add 33g (0.3mol) (R)-(-)-3-chloro-1,2-propanediol, heat to reflux overnight, cool , filtered to remove the ammonium salt, and the filtrate was evaporated to remove the methanol under reduced pressure to obtain about 71 g of the crude product of L-α-glycerophosphocholine.

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Abstract

The present invention relates to a method, which comprises that (R)-(-)-3-chloro-1,2-propanediol and a phosphocholine tetramethyl ammonium salt are subjected to a substitution reaction, and ion exchange resin purification is performed to obtain a L-alpha-choline glycerophosphate pure product. According to the present invention, the used chiral intermediate (R)-(-)-3-chloro-1,2-propanediol is further a key chiral intermediate of an antitussive agent levodropropizine, has characteristics of stable chemical property and convenient and easy obtaining, and is especially for L-alpha-choline glycerophosphate industrial production.

Description

field of invention [0001] The invention relates to the fields of chiral synthetic chemistry and medicinal chemistry, in particular to a chemical synthesis method of L-alpha-glycerophosphorylcholine. Background technique [0002] L-α-Glycerophosphoryl Choline (L-α-Glycerophosphoryl Choline, L-α-GPC) is a naturally occurring water-soluble phospholipid metabolite in the human body. L-α-GPC can pass through the blood-brain barrier and is a source of choline for the synthesis of acetylcholine and phospholecithin. It is an important neurotransmitter and phospholipid precursor. It can improve the cognitive ability and memory of the elderly and protect blood vessels. role. [0003] The structural formula of L-α-GPC is as follows: [0004] [0005] The initial method of obtaining L-α-GPC is to extract it directly from bovine pancreas (G.Schmidt, J.Biochem, 1945), or from egg yolk lecithin (GB2058792) and soybean lecithin (JP61158990) after hydrolysis The disadvantage is that th...

Claims

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Application Information

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IPC IPC(8): C07F9/10
Inventor 齐创宇马广磊徐磊杜狄峥
Owner SHANGHAI CHENPON PHARM TECH CO LTD
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