Preparation method of L-alpha-choline glycerophosphate

A technology of choline alfoscerate and phosphoryl choline, which is applied in the field of chemical synthesis of L-alpha-choline alfoscerate, which can solve the problems of unfavorable labor protection and high toxicity

Active Publication Date: 2014-03-26
天津市医药集团技术发展有限公司
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0013] CN101967160 reported that L-α-alpha-choline alphosphoric acid was obtained through the reaction of phosphorylcholine salt and 3-chloro-1,2-propanediol, but the 3-chloro-1,2-propanediol of this process has highly toxic characteristics , is a suspected carcinogen, which is not conducive to labor protection in large-scale production, and its reaction formula is as follows:

Method used

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  • Preparation method of L-alpha-choline glycerophosphate
  • Preparation method of L-alpha-choline glycerophosphate
  • Preparation method of L-alpha-choline glycerophosphate

Examples

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reference example 1

[0044] Preparation of Phosphorylcholine Sodium Salt

[0045] In the reaction bottle, add phosphorylcholine calcium salt (II) 15.00g (0.046mol) and water 75ml, stir until dissolved, add dropwise the sodium carbonate solution prepared by anhydrous sodium carbonate 9.65g and water 30ml, drop After completion, stir at room temperature for 2 hours, filter, and evaporate to dryness under reduced pressure to obtain 11.00 g of phosphorylcholine sodium salt, with a yield of 91.70% and an HPLC purity of 96.50%.

reference example 2

[0047] Preparation of Phosphorylcholine Potassium Salt

[0048]The operation was the same as in Reference Example 1, and anhydrous potassium carbonate was used instead of anhydrous sodium carbonate to obtain 12.60 g of phosphorylcholine potassium salt with a yield of 93.69% and an HPLC purity of 92.81%.

reference example 3

[0050] Preparation of Phosphorylcholine Tetramethylammonium Salt

[0051] In the reaction flask, add 15.00g (0.046mol) of phosphorylcholine calcium salt (II) and 75ml of water, stir until dissolved, add 4.05g of oxalic acid, heat up to 40°C for 4h, filter, and evaporate the filtrate to dryness under reduced pressure to obtain Dissolve the oil in 60ml of methanol, add 8.10g of tetramethylammonium hydroxide pentahydrate, react for 3h, and evaporate to dryness under reduced pressure to obtain 11.25g of phosphorylcholine tetramethylammonium salt, with a yield of 84.68% and a purity of 90.85% by HPLC.

[0052]

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Abstract

The invention discloses a preparation method of L-alpha-choline glycerophosphate. According to the method, (2S)-3-halogenated-1,2-propylene oxide and phosphoryl choline salt are used as the raw materials, and are subjected to esterification and hydrolysis reaction in a solvent to obtain the L-alpha-choline glycerophosphate crude product, and the crude product is subjected to silica gelcolumn chromatography and purification through ion exchange resin to obtain the L-alpha-choline glycerophosphate pure product. Compared with the prior art, the preparation method disclosed by the invention has the advantages that the operation is simpler; the adopted chiral material (2S)-3-halogenated-1,2-propylene oxide is cheap and easy to obtain; the prepared crude product is subjected to silica gelcolumn chromatography and purification through ion exchange resin to obtain the L-alpha-choline glycerophosphate product with higher quality, and the L-alpha-choline glycerophosphate content is more than 99%; the technical process is more suitable for large scale production.

Description

technical field [0001] The invention belongs to the technical field of chiral organic chemistry and medicine preparation, and specifically relates to a chemical synthesis method for preparing L-alpha-choline alfoscerate. Background technique [0002] L-α-Glycerophosphoryl Choline (L-α-Glycerophosphoryl Choline, L-α-GPC) is a water-soluble phospholipid metabolite naturally present in the human body. According to the patent GB2058792 report, it belongs to the cholinesterase inhibitor in the body, can pass through the blood-brain barrier, and is a necessary choline source for the synthesis of acetylcholine and phosphatidylcholine. L-α-choline alfoscerate can improve the cognitive and memory abilities of people of different ages, promote the release of growth hormone in adolescents, and indirectly help them grow taller. Japanese patent JP2009155337 reports that L-α-choline alfoscerate has anti-hyperlipidemia and blood vessel protection for the elderly, especially has a signific...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/09
Inventor 周永健赵一飞程玉红边颖孟红赵平
Owner 天津市医药集团技术发展有限公司
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