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Folic acid synthesis method

A kind of synthetic method, the technology of folic acid

Inactive Publication Date: 2016-10-26
CHANGZHOU XINHONG PHARMA & CHEM IND TECHOLOGIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantage of this method is that trichloroacetone contains a certain amount of 1,3-dichloroacetone, 1,1-dichloroacetone, 1,1,1-trichloroacetone, 1,1,1,3-tetrachloroacetone Chloroacetone, 1,1,3,3-tetrachloroacetone and 1,1,1,3,3-pentachloroacetone will also participate in the reaction, and the resulting folic acid is difficult to meet the requirements of the International Pharmacopoeia and the European Pharmacopoeia The content of pteroic acid in the finished product of folic acid is less than or equal to 0.6%
The total yield of this synthetic method is only 36.9%. α, β-dibromopropanal is unstable, expensive, and easy to decompose in the reaction system
(3) By reacting 1,1,3,3-tetramethoxy-2-propanol or 2-hydroxypropanedial with N-(4-aminobenzoyl)-L-glutamic acid to obtain the corresponding di imine, and then react with 2,4,5-triamino-6-hydroxypyrimidine sulfate in the presence of sulfite to prepare folic acid. Although the yield of this method has increased, the 1,1,3,3 -Tetramethoxy-2-propanol and 2-hydroxypropandialdehyde are expensive, difficult to produce, and unable to realize industrialization
(4) Preparation of folic acid by reaction of 2,4,5-triamino-6-hydroxypyrimidine, 1,2,3-trihalopropene, N-(4-aminobenzoyl)-L-glutamic acid and mild oxidant , the reaction uses an organic solvent, which is easy to operate and low in cost, but the raw material 2,4,5-triamino-6-hydroxypyrimidine is unstable and easily oxidized, resulting in a decrease in purity

Method used

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Embodiment 1

[0025] Embodiment 1: Synthesis of 2-amino-4-hydroxyl-6-bromomethylpteridine

[0026] Add 15.15 grams (50 mmol) of 2,4,5-triamino-6-hydroxypyrimidine dihydrogen bromide and 500 milliliters of methanol in the reaction flask, and add 12.45 grams (75 mmol) of 3-bromoacetoglyoxal to the suspension formed under stirring 100 ml of methanol solution of oxime, heated to reflux for 2.5 hours, rotary evaporation to remove about 480 ml of methanol, cooled to room temperature, stirring the residue with concentrated ammonia, and suction filtration to obtain 2-amino-4-hydroxy-6-bromomethyl The crude pteridine product was washed with methanol and dried in a vacuum oven heated to 60° C. The yield was 12.2 g, and the yield was 95%.

Embodiment 2

[0027] Embodiment 2: Synthesis of 2-amino-4-hydroxyl-6-bromomethylpteridine

[0028] Add 15.15 grams (50 mmol) of 2,4,5-triamino-6-hydroxypyrimidine dihydrogen bromide and 500 ml of 95% ethanol to the reaction flask, and add 8.30 grams (50 mmol) of 3-bromo 75 ml of 95% ethanol solution of acetone aldoxime, heated and refluxed for 3 hours, removed about 450 ml of 95% ethanol by rotary evaporation, cooled to room temperature, and the residue was neutralized with 7% sodium carbonate aqueous solution under stirring, and suction filtered to obtain 2-amino - The crude product of 4-hydroxy-6-bromomethylpteridine was washed with 95% ethanol, and dried in a vacuum oven heated to 70° C. The yield was 11.14 g, and the yield was 87%.

Embodiment 3

[0029] Example 3: Synthesis of 2-amino-4-hydroxyl-6-chloromethylpteridine

[0030] Add 10.70 grams (50 mmol) of 2,4,5-triamino-6-hydroxypyrimidine dihydrochloride and 450 milliliters of methanol to the reaction flask, and add 9.11 grams (75 mmol) of 3-chloroacetone aldoxime to the suspension formed under stirring 90 ml of methanol solution, heated to reflux for 3 hours, rotary evaporated to remove about 420 ml of methanol, cooled to room temperature, stirred, the residue was neutralized with concentrated ammonia water, and suction filtered to obtain 2-amino-4-hydroxyl-6-chloromethyl The crude product of pteridine was washed with methanol and dried in a vacuum oven heated to 60° C. The yield was 9.42 g, and the yield was 89%.

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Abstract

The present invention relates to a folic acid synthesis method. According to the present invention, with the method, a 2,4,5-triamino-6-hydroxypyrimidine salt, 3-halogenated pyruvaldehyde oxime and N-(4-aminobenzamide)-L-glutamic acid are subjected to a reaction to prepare the folic acid; and the 3-halogenated pyruvaldehyde oxime is used to replace the low purity 1,1,3-trichloroacetone, such that the generation of a large amount of waste water in the traditional method is avoided, the reaction conditions are mild, the operation is easy, the reaction selectivity is good, the product purity is high, the advantages of safety and environmental protection are provided, and the method is suitable for the industrial requirements on environmental protection.

Description

technical field [0001] The invention belongs to the technical field of vitamins, and in particular relates to a method for synthesizing folic acid with less waste water, in particular to a method utilizing 3-haloacetone aldoxime, 2,4,5-triamino-6-hydroxypyrimidine salt and N-( A new method for the preparation of folic acid by the reaction of 4-aminobenzoyl)-L-glutamic acid. Background technique [0002] Folic acid belongs to the basic variety of vitamins and is an anti-anemia drug, which is used in feed, medicine and food and other fields. It is used as an anti-anemia drug additive in the feed industry. When folic acid is lacking, it will cause anemia, loss of appetite, growth retardation, leukopenia and other diseases in animals, which will hinder the growth of animals and cause poor feather development. With the rapid development of animal husbandry, the demand for folic acid is also increasing rapidly. The health function of folic acid in medicine and food is gradually ...

Claims

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Application Information

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IPC IPC(8): C07D475/04
CPCC07D475/04
Inventor 王国华张继振王胜忠
Owner CHANGZHOU XINHONG PHARMA & CHEM IND TECHOLOGIES
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