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Preparation method of benfotiamine intermediate monophosphothiamine

A technology of benfotiamine and an intermediate, which is applied in the field of organic compound preparation technology, can solve the problems of being unsuitable for industrial scale production, low production efficiency, slow cycle process and the like, and achieves a short production cycle, less waste water and less environmental pollution. Effect

Inactive Publication Date: 2020-03-24
SHANGHAI RIXIN BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Purpose of the invention: the purpose of the present invention is to provide a preparation method of phostiamine, an intermediate of benfotiamine, which solves the problem that the existing phostiamine production method has a slow cycle process, low production efficiency, serious pollution, and is not suitable for industrial scale production. question

Method used

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  • Preparation method of benfotiamine intermediate monophosphothiamine
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  • Preparation method of benfotiamine intermediate monophosphothiamine

Examples

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Effect test

Embodiment 1

[0018] Add 21.1 (0.106mol) grams of pyrophosphoric acid and 100.0 grams of toluene in the reaction flask with a mass ratio of 90%, and heat to 80°C. When the temperature in the reaction flask reaches 80°C, add 10.0 grams (0.0265mol) of compound 1 in batches , react at a temperature of 80°C for 2 hours, also at 80°C, add 10.0 g (0.106 mol) of hydrochloric acid solution, maintain 80°C and stir for 1.0 hour, drop to room temperature and separate layers, take the lower layer containing the product and put it in a clean reaction bottle, Add ethanol dropwise to the reaction bottle, filter after crystallization, rinse the filtered solid with 5 mL of ethanol, and dry to obtain 12.4 g of phostiamine, moisture: 1.2%, purity: 96.25%.

Embodiment 2

[0020] Add 21.1 (0.106mol) grams of pyrophosphoric acid and 100.0 grams of chlorobenzene in the reaction flask, and heat it to 80°C. When the temperature in the reaction flask reaches 80°C, add 10.0 grams (0.0265mol) of the compound in batches 1. After reacting at 93°C for 2 hours, cool down to 80°C; add 10.0 g (0.106 mol) of hydrochloric acid solution, keep stirring at 80°C for 1.0 hour, drop to room temperature and separate layers, take the lower layer containing the product and put it in a clean reaction bottle During the process, ethanol was added dropwise to the reaction bottle, and after crystallization, it became oily solid phostiamine, which could not be filtered.

Embodiment 3

[0022] Add 21.1 grams (0.106mol) of pyrophosphoric acid with a mass ratio of 90% and 100.0 grams of toluene to the reaction flask, and heat it to 80°C. When the temperature in the reaction flask reaches 80°C, add 10.0 grams (0.0265mol) of compound 1 in batches , after reacting at 95°C for 2 hours, cool down to 80°C; add 10.0 g (0.106 mol) of hydrochloric acid solution, keep stirring at 80°C for 1.0 hour, drop to room temperature and separate layers, take the lower layer containing the product and put it in a clean reaction bottle , add acetone dropwise to the reaction flask, filter after crystallization, rinse the filtered solid with 5 mL of acetone, and dry to obtain 11.4 g of phostiamine, moisture: 1.8%, purity: 93.5%.

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Abstract

The invention discloses a preparation method of benfotiamine intermediate monophosphothiamine. The preparation method comprises the steps: adding pyrophosphoric acid and a diluent into a reaction flask, heating to 80 DEG C, and adding a compound 1 in batches; carrying out a reaction for 2-3 hours at the temperature of 80-100 DEG C, and cooling to 80 DEG C; and adding hydrochloric acid, stirring for 1 hour, cooling to room temperature, layering, taking a lower layer, putting into a clean reaction bottle, dropwise adding an organic solution into a bottle, crystallizing, and filtering to obtain acompound 2, namely the key intermediate monophosphothiamine. The method is short in production period, simple to operate, less in wastewater, less in environmental pollution, simple and convenient inprocess and easy for industrial production.

Description

technical field [0001] The invention relates to the technical field of organic compound preparation technology, in particular to a method for preparing a benfotiamine intermediate, phostiamine. Background technique [0002] Benfotiamine is a fat-soluble derivative of thiamine, a synthetic vitamin B1 derivative that is slightly soluble in water. Synthesized in Japan in the 1960s, it was gradually used in the treatment of neuropathy, sciatica and other neuropathic pains caused by alcoholism after 1962. Since the 1990s, European scholars have conducted a series of studies on thiamine, especially benfotiamine, in the treatment and prevention of diabetes and its complications, and have made significant progress in recent years. The drug has been used in Europe for more than a decade to treat various conditions, including nerve damage associated with diabetes. Benfotiamine was developed by Akira, a Japanese company. The chemical name of Benfotiamine is S-[2-[[(4-amino-2-methyl-5...

Claims

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Application Information

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IPC IPC(8): C07F9/6558
CPCC07F9/65583
Inventor 葛敏陈怡唐静
Owner SHANGHAI RIXIN BIOTECHNOLOGY CO LTD
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