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Synthesis method of phosphate monoester of vitamin B1

A phosphate monoester and synthesis method technology, applied in the field of preparation of pharmaceutical intermediates, can solve the problems of high energy consumption, large solid waste, etc., and achieve the effect of simple operation, reduced dosage, and suitable for industrial production

Active Publication Date: 2015-06-24
暨明医药科技(苏州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, a large amount of water must be added to stir the reaction solution, resulting in the final concentration of a large amount of water, high energy consumption, and a large amount of solid waste

Method used

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  • Synthesis method of phosphate monoester of vitamin B1
  • Synthesis method of phosphate monoester of vitamin B1

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] In a 1 L three-necked flask, add 50.0 g of vitamin B1, 106.1 g of phosphoric acid (5 times the mole), 42.0 g of phosphorus pentoxide (2 times the mole) and 100 ml of chlorobenzene (2 times the volume), at 110°C to 150 ℃ heating to reflux and stirring for 6-10 hours. Cool to room temperature, add 150 ml of water, and then add 219.5 g of calcium hydroxide (20 times the molar weight) to neutralize the phosphoric acid as a solid, and filter under reduced pressure to remove the white solid. Liquid separation obtains water layer, adds 400 ml acetone, separates out white solid, and drying under reduced pressure obtains white solid powder 40 g, and yield is 65%, and HPLC purity is 98%.

Embodiment 2

[0021] In a 1 L three-necked flask, add 40 g of vitamin B1, 42.4 g of phosphoric acid (2.5 times the molar weight), 16.9 g of phosphorus pentoxide (1 times the molar weight) and 80 ml of chlorobenzene (2 times the volume), at 110 ° C to 150 ℃ heating to reflux and stirring for 6-10 hours. Cool to room temperature, add 80 ml of water, and then add 133.0 g of calcium carbonate (10 times the molar weight) solid to neutralize phosphoric acid to neutral, and filter under reduced pressure to remove the white solid. Liquid separation obtains water layer, adds 200 ml acetone, separates out white solid, and drying under reduced pressure obtains white solid powder 30.2 g, and yield is 61%, and HPLC purity is 98%.

Embodiment 3

[0023] In a 1 L three-necked flask, add 50.0 g of vitamin B1, 21.2 g of phosphoric acid (1 times the mole), 10.5 g of phosphorus pentoxide (0.5 times the mole) and 50 ml of chlorobenzene (1 times the volume), at 110°C to 150 ℃ heating to reflux and stirring for 6-10 hours. Cool to room temperature, add 100 ml of water, and then add 54.9 g of calcium hydroxide (5 times the molar amount) to neutralize the phosphoric acid to neutrality, and filter under reduced pressure to remove the white solid. Liquid separation was obtained water layer, added 300 ml ethanol, separated out white solid, dried under reduced pressure to obtain white solid powder 20 g, yield was 32%, and HPLC purity was 95%.

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Abstract

The invention discloses a synthesis method of a phosphate monoester of vitamin B1, which comprises the following steps of: using the vitamin B1 as a starting raw material, adding an organic solvent as a diluent, using phosphoric acid and phosphorus pentoxide as esterification reagents to be subjected to an esterification reaction; then undergoing hydrolysis, and then adding an alkali metal salt to neutralize the phosphoric acid to be neutral; and finally, undergoing crystallization and drying to obtain the phosphate monoester of vitamin B1. According to the synthesis method of the phosphate monoester of vitamin B1, the organic solvent is used as the diluent, the amount of the phosphoric acid is reduced, the amount of the alkali metal salt is reduced, the solid waste is reduced, the energy consumption is saved, and the environmental protection is favorable; and meanwhile, the method has a simple operation route and no complex post-treatment process, and is more suitable for industrial production.

Description

technical field [0001] The invention relates to the field of preparation of pharmaceutical intermediates, in particular to a method for synthesizing vitamin B1 phosphate monoester. Background technique [0002] Vitamin B1 is irreplaceable as medicine and nutrition. Vitamin B1 helps the human body digest, relieve fatigue, maintain normal activity of the nervous system, relieve symptoms of motion sickness and seasickness, and help treat beriberi, especially in the treatment of nervous disorders and diabetic neuropathy. Water-soluble vitamin B1 is not easily absorbed by the human body. If the human body takes in more than 12 mg of vitamin B1, the concentration of vitamin B1 in the plasma will no longer increase. In order to achieve therapeutic effects, high concentrations of vitamin B1 are required in the blood and tissues. For a long time, people have hoped to find compounds that are more easily absorbed by the body to replace vitamin B1. In 1954, Fujiwara discovered a grou...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6558
Inventor 李斌峰孙涛
Owner 暨明医药科技(苏州)有限公司