Method of preparing L-alpha-glycerol phosphatidylcholine

A technology of glycerol phosphatidylcholine and phosphorylcholine, which is applied in the field of medicine and chemical industry, can solve the problems of low yield and long reaction time of L-α-alphaphosphocholine, and achieve easy industrial production, high purity, The effect of high total reaction yield

Active Publication Date: 2018-06-01
湖南华纳大药厂手性药物有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But this method prepares L-alpha-choline alfoscer

Method used

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  • Method of preparing L-alpha-glycerol phosphatidylcholine
  • Method of preparing L-alpha-glycerol phosphatidylcholine
  • Method of preparing L-alpha-glycerol phosphatidylcholine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Preparation of (R)-2-methoxy-4-chloromethyl-1,3-dioxocyclopentane.

[0076] In a 500mL glass bottle, weigh 115.5g (1.0 mole) of (R)-3-chloroglycerol, 138.0g (1.3 mole) of trimethyl orthoformate, and 19.0g p-toluenesulfonic acid. After mixing, stir and heat to React at 70-90°C. During the reaction, low-boiling materials are distilled from the distillation head, mainly methanol and a small amount of methyl formate. The progress of the reaction was detected by GC, and the reaction was complete in about 6 hours. After the reaction is complete, cool to room temperature, add sodium methoxide to neutralize to pH=6-7. First heat and depressurize to recover the low boiling point solvent, and then collect the 102-105°C fraction at -0.096Mpa to obtain 143.4g of the product with a yield of 91%.

Embodiment 2

[0078] Preparation of (R)-2-ethoxy-4-chloromethyl-1,3-dioxocyclopentane.

[0079] In a 500mL glass bottle, weigh 115.5g (1.0 mole) of (R)-3-chloroglycerol, 192.5g (1.3 mole) of triethyl orthoformate, and 19.0g p-toluenesulfonic acid. After mixing, stir and heat to React at 70-90°C. During the reaction, low-boiling materials are distilled from the distillation head, mainly ethanol and a small amount of ethyl formate. The progress of the reaction was detected by GC, and the reaction was complete in about 8 hours. After the reaction is complete, cool to room temperature, add sodium ethoxide to neutralize to pH=6-7. First heat and depressurize to recover the low boiling point solvent, and then collect the 114-116°C fraction at -0.096Mpa to obtain 154.5g of the product with a yield of 90%.

Embodiment 3

[0081] Preparation of (R)-2-methoxy-4-bromomethyl-1,3-dioxocyclopentane.

[0082] In a 500mL glass bottle, weigh 199.0g (1.0 mole) of (R)-3-bromoglycerol, 138.0g (1.3 mole) of trimethyl orthoformate, and 19.0g p-toluenesulfonic acid. After mixing, stir and heat to React at 70-90°C. During the reaction, low-boiling materials are distilled from the distillation head, mainly methanol and a small amount of methyl formate. The progress of the reaction was detected by GC, and the reaction was complete in about 6 hours. After the reaction is complete, cool to room temperature, add sodium methoxide to neutralize to pH=6-7. First heat and depressurize to recover the low boiling point solvent, and then collect the 68-73°C fraction at about 100pa to obtain 177.8g of product with a yield of 88%.

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Abstract

The invention provides a method of preparing L-alpha-glycerol phosphatidylcholine. The method includes the steps of: 1) performing a reaction to halogenated glycerol and ester under catalysis by an acid to produce a halogenated glycerol double-hydroxyl-protected substance I; 2) performing a reaction to phosphatidylcholine salt with the halogenated glycerol double-hydroxyl-protected substance I toobtain an L-alpha-glycerol phosphatidylcholine double-hydroxyl-protected substance II crude product; 3) separating the L-alpha-glycerol phosphatidylcholine double-hydroxyl-protected substance II fromthe non-reacted halogenated glycerol double-hydroxyl-protected substance I to obtain pure L-alpha-glycerol phosphatidylcholine double-hydroxyl-protected substance II; 4) performing deprotective reaction under catalysis by acid in catalytic amount to the pure L-alpha-glycerol phosphatidylcholine double-hydroxyl-protected substance II to obtain a water solution of the L-alpha-glycerol phosphatidylcholine, and performing pressure-reduced evaporation to remove water and performing crystallization with an alcohol solvent to obtain the L-alpha-glycerol phosphatidylcholine. The method, compared withthe prior art, is high in purity and yield and is suitable for industrial production.

Description

Technical field: [0001] The invention relates to the technical field of medicine and chemical industry, in particular to a preparation method of L-alpha-glycerol phosphatidylcholine. Background technique: [0002] L-α-glycerolphosphatidylcholine (L-alpha-Glycerphosphatidylcholine, referred to as GPC) is an active substance that can improve brain function, and has a certain effect on the prevention and auxiliary treatment of senile dementia. [0003] There are two known technical means for obtaining GPC: one is extraction from natural products, such as extracting egg yolk lecithin from egg yolk, and extracting soybean lecithin from soybeans. Further separation and purification by chemical or enzymatic hydrolysis to obtain GPC (such as US5250719, US5315023, US6274362, EP217765, etc.). [0004] The second method is obtained by chemical synthesis. [0005] Obtaining from natural products has different variables due to different sources of raw materials and origins, the process...

Claims

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Application Information

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IPC IPC(8): C07F9/10
CPCC07F9/10
Inventor 皮士卿谭跃李乐欢刘庆林傅裕黄本东徐燕
Owner 湖南华纳大药厂手性药物有限公司
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