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Method for synthesizing beta-sodium glycero-phosphate

A technology of sodium glycerophosphate and a synthesis method is applied in the field of synthesis of a phosphorus deficiency treatment agent or a nutritional medicine for phosphorus supplementation, and can solve the problems of only microgram level of separation and difficulty in industrial application, etc.

Inactive Publication Date: 2009-11-11
SHANGHAI INNOVATIVE RESEARCH CENTER OF TRADITIONAL CHINESE MEDICINE
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method is to synthesize β-glycerophosphate instead of β-sodium glycerophosphate, and this method also has a significant disadvantage: when hydrolyzed with barium hydroxide aqueous solution, 80% of β-glycerophosphate is converted into α- Glycerophosphate, so this method actually synthesizes the method for the mixture of α-glycerophosphate and β-glycerophosphate, and the reaction formula is as follows:
[0005] In January 1957, Chieko Urakami and Yoshiko Kakutani reported the separation of α-sodium glycerophosphate and β-sodium glycerophosphate by paper chromatography in Bulletinof the chemical Society of Japan, (1957), 30, 21-5, but the separation amount Only at the microgram level; in June 1957, Chieko Urakami et al. reported the separation of α-sodium glycerophosphate and β-sodium glycerophosphate by column chromatography (Bulletin of the chemical Society of Japan, (1957), 30, 379-81.) , but there is only milligram-level separation, and it is very difficult to achieve industrial applications; in 1999, Marinescu, Marin reported the method of synthesizing sodium glycerophosphate with glycerol and disodium hydrogen phosphate in aqueous solution (Rom 114618B3), but the product obtained It is also a mixture of α-sodium glycerophosphate and β-sodium glycerophosphate, and the method of directly synthesizing β-sodium glycerophosphate has not been reported

Method used

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  • Method for synthesizing beta-sodium glycero-phosphate
  • Method for synthesizing beta-sodium glycero-phosphate

Examples

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Embodiment 1

[0019] Example 1 1, the synthesis of 3-dibenzyloxy (or substituted benzyloxy)-2-propoxyphosphoric acid (III)

[0020] 1,3-dibenzyloxy (or substituted benzyloxy)-2-propanol (I) 54.4 g (0.20 mol) was dissolved in 200 ml of methylene chloride, 39.5 g of pyridine was added, cooled to -10°C 153.5 grams of phosphorus oxychloride was added dropwise under stirring, and after stirring for 1 hour at -10°C, it was allowed to rise naturally to room temperature and stirred for 3 hours. Stir for 1 hour, extract with 200 ml of ethyl acetate, wash the organic phase successively with 5% aqueous sodium bicarbonate solution, saturated brine, dry over anhydrous magnesium sulfate, evaporate the solvent to obtain 56.3 g of light yellow transparent liquid, yield: 80%. MS: 350.9 (ESI), HNMR: 7.20-7.25 (m, 10H), 5.42-5.45 (d, 4H), 3.61-3.64 (dd, 4H).

Embodiment 2

[0021] The synthesis of embodiment 2 β-sodium glycerophosphate

[0022] 1,3-Dibenzyloxy (or substituted benzyloxy)-2-propoxyphosphoric acid (III) 167 grams (0.47mol) was dissolved in 1200 ml of ethyl acetate, added to a 2-liter autoclave, and 8.3 grams of 10% palladium carbon, hydrogen replacement 3 times, hydrogen pressure added to 50 atmospheres, stirred at 50 ° C for 20 hours, added 500 ml of water, the aqueous layer was extracted 3 times with ethyl acetate (200 ml x 3), the aqueous layer Adjust Ph=9, remove most of the water by distillation under reduced pressure, freeze-dry the raffinate to obtain 125 grams of crude product of β-glycerophosphate sodium, recrystallize to obtain 115 grams of white crystals, yield 80%, content 99% (HPLC, external standard method ). Na: 21.75%, P: 14.70.%.

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Abstract

A method for synthesizing beta-sodium glycero-phosphate comprises the following steps: performing phosphorylation to 1,3-dibenzyloxy (or substituted benzyloxy)-2-propanol to form phosphate ester; removing a protecting group; and neutralizing the 1,3-dibenzyloxy (or substituted benzyloxy)-2-propanol with alkali to obtain the beta-sodium glycero-phosphate. The method has the advantages of cheap raw materials, easy acquisition, mild reaction condition, high product yield, no alpha-sodium glycero-phosphate in the product, no need of separation purification by column chromatography in the whole synthesis step, easy and convenient operation, less equipment investment and low cost. Therefore, the synthesis method is suitable for industrial large-scale production.

Description

technical field [0001] The invention relates to a synthesis method of a phosphorus deficiency treatment agent or a nutritional medicine for phosphorus supplementation, in particular to a synthesis method of β-glycerophosphate sodium. Background technique [0002] Sodium glycerophosphate, which is a mixture of α-sodium glycerophosphate and β-sodium glycerophosphate, has been included in the Pharmacopoeia of the People's Republic of China (2005 Edition, Part II) as a phosphorus supplement drug, and is used for the prevention and treatment of osteoporosis disease, osteomalacia, etc. Sodium beta-glycerophosphate can be used alone. [0003] Through literature search, the process of synthesizing pure sodium β-glycerophosphate has not been reported, only relevant literature reports. 1950, Viscontin, M; Pudles, J.HelveticaChimica Acta (1950), 33,594-5, reported the synthesis method of β-glycerophosphate, this method is 1,3-diacetoxy-2-propanol In pyridine, react with phosphorus o...

Claims

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Application Information

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IPC IPC(8): C07F9/10A61P19/10
CPCY02P20/55
Inventor 郭峰段利枝杨志奇杨子荣滕继军袁凌睿
Owner SHANGHAI INNOVATIVE RESEARCH CENTER OF TRADITIONAL CHINESE MEDICINE
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