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One-step method for preparing raceme DL, D or L-a-glycerin phosphorus acyl choline

A technology for glycerol phosphoryl choline and phosphoryl choline, which is applied in directions such as phosphorus organic compounds, can solve the problems of complicated process steps, unsuitable for industrialized production and the like, and achieves the effect of simple operation

Active Publication Date: 2011-02-09
SUZHOU FUSHILAI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] Korean patent KR2009 / 39132 protects the hydroxyl group of glycidol with benzyl group and then opens the ring, and protects the 1 and 2 hydroxyl groups with acetyl group. It seems that the process steps are more complicated, and sodium hydrogen and palladium carbon are also used in the process. Synthetic method, not suitable for industrial production

Method used

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  • One-step method for preparing raceme DL, D or L-a-glycerin phosphorus acyl choline
  • One-step method for preparing raceme DL, D or L-a-glycerin phosphorus acyl choline
  • One-step method for preparing raceme DL, D or L-a-glycerin phosphorus acyl choline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] In a 500 ml four-necked reaction flask, add 135 ml of water, start stirring and add 30 g of phosphorylcholine chloride calcium salt (containing 4 crystal water), after all dissolve, add 9.75 g of anhydrous sodium carbonate and 90 ml of water dropwise at room temperature The sodium carbonate solution made, the dropping time is controlled at 30~45 minutes, stir at room temperature for 1.0 hour after dropping, filter, the filter cake is washed with 20ml of water, the washing liquid is incorporated into the filtrate, and placed in a reaction flask under reduced pressure below Evaporate the water to dryness at 60 degrees to obtain a white solid, add 240 milliliters of absolute ethanol, stir and add 14 grams of R-3-bromo-1,2-propanediol, heat up and make it reflux until the TLC reaction is completed, ( The reaction formula of the synthesis reaction is shown above) cooling, filtering, washing the filter cake with a small amount of ethanol, combining the filtrates, distilling th...

Embodiment 2

[0028] In the same manner as in Example 1, 14 grams of R-3-bromo-1,2-propanediol was changed to 10 grams of R-3-chloro-1,2-propanediol to obtain 18.3 grams with an optical rotation of -2.7° and a purity of over 99.48%. White L-α-GPC crystals.

Embodiment 3

[0030] Change 30 grams of phosphorylcholine calcium salt into 17 grams of phosphorylcholine according to Example 1, add 2 grams of sodium hydroxide after being dissolved in water, add R-3-chlorine 1,2-propanediol dropwise after becoming a clear liquid, and Operation method (that is, the same as in Example 1, the same below) can finally obtain 18.6 grams of GPC, with an optical rotation of -2.6° and a purity of 99.38% white L-α-GPC crystal.

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Abstract

The invention provides a one-step method for preparing raceme DL, D or L-a-glycerin phosphorus acyl choline, belonging to the technical field of the perpetration of the chiral organic chemistry and the medicine. The method comprises the following steps of: taking 3-halogenated-1, 2-propylene glycol as raw material, and leading the 3-halogenated-1, 2-propylene glycol to be reacted with the phosphorus acyl choline or the phosphorus acyl choline salt to obtain the raceme DL, D or the L-a-glycerin phosphorus acyl choline. Compared with the prior art, the technical scheme is simpler in operation, can obtain the raceme DL, D or the L-a-glycerin-GPC only by one step, and can obtain the ideal yield and purity. The GPC yield is more than 75%, the purity is more than 99%, and the optical rotation is -2.4 to -3.0 degrees.

Description

technical field [0001] The invention belongs to the technical field of chiral organic chemistry and medicine preparation, and specifically relates to a method for preparing racemate DL, D or L-alpha-glycerophosphorylcholine in one step. Background technique [0002] The racemate DL, D or L-α-glycerophosphatylcholine is generally referred to as α-glycerophosphatidylcholine (English name: Alpha-Glycerphosphatidylcholine, abbreviated as α-GPC). GPC is an active substance that can improve brain function. Because it has a very good effect on the treatment of cerebrovascular attacks and senile degenerative brain disease syndrome, it has been widely used in the clinical treatment of senile dementia. In recent years, it has also been reported that it has been used in formulas for treating chronic obstructive pulmonary disease, osteoporosis, hair growth restoration agent and anti-fatigue, anti-hypertension, anti-diabetes and anti-depression (see JP2009 / 155337), Therefore, the techni...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/09
Inventor 丁建飞陆定熙腾明清金育岐石晓峰邢健钱庆邵敏石晓青顾晔浦佳春陆建刚谭雪良
Owner SUZHOU FUSHILAI PHARMA CO LTD
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