A kind of industrial manufacturing method of glycerophosphocholine

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

Active Publication Date: 2017-02-22
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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  • A kind of industrial manufacturing method of glycerophosphocholine
  • A kind of industrial manufacturing method of glycerophosphocholine
  • A kind of industrial manufacturing method of glycerophosphocholine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Add phosphoryl choline calcium salt (generally tetrahydrate) 330g and 300ml water in reactor, stir until dissolving clear, drip the concentration that is made of anhydrous sodium carbonate 106g and water be the sodium carbonate solution of 50%, Add dropwise at a rate of 10ml / min. After the drop is complete, stir at room temperature for 1 hour. According to the different solubility of sodium chloride, separate out the sodium chloride in the reaction system by salting out and filter.

[0047] The filtrate was passed through a sulfonic acid-type ion column, and eluted with water several times until no product was found in HPLC.

[0048] 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 that there was no raw material, the water was evaporated under reduced pressure, and recrystallized in methanol to obtain 289g product. (HPLC>99.7%)

Embodiment 2

[0050] Add phosphorylcholine calcium salt (generally tetrahydrate) 330g and 200ml water in the reaction kettle, stir until dissolving clear, add dropwise the potassium carbonate solution that the concentration that is made of potassium carbonate 138g and water is 35%, with 5ml Add dropwise at a speed of 1 / min, after the drop is completed, stir at room temperature for 0.5 hour, pass through a silica gel column to remove inorganic salt insolubles such as potassium chloride.

[0051] The filtrate was passed through a sulfonic acid-type ion column, eluted with methanol several times until there was no product in HPLC, and evaporated under reduced pressure until there was no distillate.

[0052] Add 300ml of 1,2-dimethoxyethane to dissolve the above substances, stir and drop 66g of (R)-chiral glycidol, and reflux for 8 hours. HPLC shows that there is no raw material, and the water is evaporated under reduced pressure to obtain 291g of product. (HPLC>99.5%)

Embodiment 3

[0054] Add 330g of phosphorylcholine calcium salt (generally tetrahydrate) and 500ml of water into the reaction kettle, stir until it dissolves, add dropwise a 65% sodium oxalate solution made of 133g of sodium oxalate and water, and add 2ml Add dropwise at a speed of 1 / min, after the drop is complete, stir at room temperature until no new precipitation occurs. According to the different solubility of sodium chloride, the sodium chloride in the reaction system is precipitated by salting out and then filtered.

[0055] The filtrate was passed through a sulfonic acid-type ion column, and eluted with 1,2-dimethoxyethane several times until no product was found in HPLC.

[0056] Concentrate to 400ml, stir and add 66g of (R)-chiral glycidol dropwise, and reflux for 7 hours. HPLC shows that there is no raw material, and the water is evaporated under reduced pressure to obtain 295g of 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 in particular relates to an industrial production method of glycerophosphocholine. Background technique [0002] Alzheimer's disease, also known as Alzheimer's disease (Alzheimer's disease, AD), is a primary degenerative brain disease that occurs in old age and early old age. In this state, there are obstacles in memory, thinking, analysis and judgment, visuospatial recognition, emotion, etc. Its characteristic pathological changes are atrophy of the cerebral cortex, accompanied by deposition of β-amyloid protein, neurofibrillary tangles, loss of a large number of memory neurons, and formation of senile plaques. There are currently no therapeutic drugs that can specifically treat or reverse disease progression. It is also one of the four common neurodegenerative diseases (the other three are Huntington's disease, Lou Gehrig's disease, and Parkinson's disease). [0003] Researching and find...

Claims

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Application Information

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Patent Type & Authority Patents(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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