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Industrial manufacturing method of glycerol phosphocholine

A technology of glycerophosphocholine and industrial manufacturing, applied in the direction of phosphorus organic compounds, can solve the problems of high cost, difficult purification, complicated reaction, etc., and achieve the effect of avoiding by-product problems and purification problems

Active Publication Date: 2015-05-20
上海旺客化学品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, at present, the synthesis of this substance often has problems such as high cost, complicated reaction, and difficult purification.

Method used

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  • Industrial manufacturing method of glycerol phosphocholine
  • Industrial manufacturing method of glycerol phosphocholine
  • Industrial manufacturing method of glycerol phosphocholine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Add 330g of phosphorylcholine calcium salt (usually tetrahydrate) and 300ml of water into the reaction kettle, stir until it is clear, and add dropwise a 50% sodium carbonate solution made of 106g anhydrous sodium carbonate and water. Add dropwise at a rate of 10ml / min, after dropping, stirring at room temperature for 1 hour, according to the different solubility of sodium chloride, the sodium chloride in the reaction system is precipitated by salting out and then filtered.

[0046] The filtrate was passed through a sulfonic acid ion column and eluted with water several times until there was no product in HPLC.

[0047] The solvent was distilled under reduced pressure, concentrated to a volume of 300ml, 66g of (R)-chiral glycidol was added, stirred and refluxed for 2-6 hours, HPLC showed no raw materials, evaporated under reduced pressure to remove water, recrystallized in methanol to obtain 289g product. (HPLC>99.7%)

Embodiment 2

[0049] Add 330g of phosphorylcholine calcium salt (generally tetrahydrate) and 200ml of water into the reaction kettle, stir until it dissolves, and add dropwise a 35% potassium carbonate solution made of 138g of potassium carbonate and water to 5ml Add dropwise at a rate of 1 / min, after dropping, stir at room temperature for 0.5 hours, and pass through a silica gel column to remove potassium chloride and other insoluble inorganic salts.

[0050] The filtrate was passed through a sulfonic acid ion column, eluted with methanol several times until there was no product in HPLC, and evaporated under reduced pressure until there was no distillate.

[0051] 300ml of 1,2-dimethoxyethane was added to dissolve the above substances, 66g of (R)-chiral glycidol was added dropwise with stirring, and the reaction was refluxed for 8 hours. HPLC showed that there was no raw material, and the water was evaporated under reduced pressure to obtain 291g of product. (HPLC>99.5%)

Embodiment 3

[0053] Add 330g of phosphorylcholine calcium salt (generally tetrahydrate) and 500ml of water into the reaction kettle, stir until it is clear, and add dropwise a 65% sodium oxalate solution made up of 133g of sodium oxalate and water, with 2ml Add dropwise at a rate of 1 / min. After dropping, stir at room temperature until no new precipitation is generated. According to the solubility of sodium chloride, the sodium chloride in the reaction system is separated out by salting out and then filtered.

[0054] The filtrate was passed through a sulfonic acid ion column and eluted with 1,2-dimethoxyethane several times until there was no product in HPLC.

[0055] Concentrate to 400ml, add 66g of (R)-chiral glycidol dropwise with stirring, and react under reflux for 7 hours. HPLC shows that there is no raw material. The water is evaporated under reduced pressure to obtain 295g product. (HPLC>99.5%)

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Abstract

The invention provides an industrial manufacturing method of glycerol phosphocholine. The industrial manufacturing method is characterized by comprising the following steps of reacting a compound A as a raw material and sodium salt or potassium salt to produce a compound B, carrying out ion exchange to produce a compound C and reacting the compound C and glycidol to produce glycerol phosphocholine. The method can be continuously completed in a one-pot process, step-by-step purification process of intermediate products is not needed, foreign reagents such as a catalyst do not need to be added, the final pure product can be obtained by only removing the reaction solvent, the operation is extremely convenient, the raw materials are low in cost and the yield can be not less than 90%.

Description

Technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to an industrial manufacturing method of glycerophosphocholine. Background technique [0002] Alzheimer’s disease, also known as Alzheimer’s disease (AD), is a primary degenerative encephalopathy that occurs in the old and pre-senile period. It is a persistent high-level neurological disorder, that is, when there is no disturbance of consciousness In the state of circumstance, there are obstacles in memory, thinking, analysis and judgment, visual space recognition, emotions, etc. Its characteristic pathological changes are cerebral cortex atrophy, accompanied by β-amyloid protein deposition, neurofibrillary tangles, a reduction in the number of a large number of memory neurons, and the formation of senile plaques. At present, there is no specific treatment or therapeutic drugs to reverse disease progression. It is also one of the four most common neurodegenerative diseases (...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/09
Inventor 王志训
Owner 上海旺客化学品有限公司
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