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Folic acid synthesis method

A synthetic method and technology of folic acid, applied in organic chemistry and other fields, can solve problems such as cumbersome post-treatment process, avoid the use of a large amount of hydrochloric acid, have mild reaction temperature, and reduce environmental pollution

Pending Publication Date: 2021-12-21
北京斯利安药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the post-treatment process of each step of this method is relatively cumbersome, and the intermediate product needs to be separated or purified before the next reaction can be carried out.

Method used

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preparation example Construction

[0041] The embodiment of the present invention provides a folic acid synthesis method, comprising the following steps:

[0042] mixing p-nitrobenzoyl chloride and L-glutamic acid in water, performing a condensation reaction at a pH of 10 to 11, and separating the water phase in the product obtained by the condensation reaction;

[0043] The aqueous phase, ammonium formate and palladium carbon are subjected to a reduction reaction and then the palladium carbon is removed to obtain a reduced product;

[0044] The reduction product, 2,4,5-triamino-6-hydroxypyrimidine sulfate, 1,1,3-trichloroacetone and pyrosulfous acid are subjected to ring closure reaction under the condition of pH=2-4.

[0045] In some embodiments, in terms of molar ratio, the amount of reaction raw materials added is p-nitrobenzoyl chloride and L-glutamic acid=1: (1-1.1).

[0046] In some embodiments, based on the molar ratio, the addition amount of the reaction raw materials is p-nitrobenzoyl chloride and am...

Embodiment 1

[0067] Put 17.44g (0.12mol) L-glutamic acid and 80mL water into a 500ml reaction bottle, stir and cool down to 5°C, add dropwise a 15% sodium hydroxide solution until the reaction system dissolves, and then simultaneously add p-Nitrate The toluene solution of p-nitrobenzoyl chloride (20.00g (0.11mol) p-nitrobenzoyl chloride is dissolved in 80ml toluene), pH=10 is controlled, and the reaction is dripped for 2h. Phase HPLC intermediate 1 purity 99.46%.

[0068] Put the water phase into a 500ml reaction flask, then add 27.20g (0.43mol) of ammonium formate and 1.28g of palladium carbon, stir and heat up to 50±5°C, react for 3h, filter off palladium carbon, the purity of HPLC intermediate 2 of the filtrate is 99.14 %.

[0069] Put the filtrate into a 1000ml reaction flask, add 600ml of water, under stirring, adjust the pH to 3 ± 0.5 with concentrated hydrochloric acid, then add 30.94g of 2,4,5-triamino-6-hydroxypyrimidine sulfate (0.13mol), 79.53g of 1,1,3-trichloroacetone (0.49m...

Embodiment 2

[0071] Put 15.86g of L-glutamic acid (0.11mol) and 80mL of water into a 500ml reaction bottle, stir and cool down to 10°C, add dropwise a 15% sodium hydroxide solution until the reaction system dissolves, and then add p-Nitrate dropwise at the same time Toluene solution of p-nitrobenzoyl chloride (20.00g p-nitrobenzoyl chloride dissolved in 80ml toluene), control pH = 11, drop the reaction for 2h, leave the reaction solution to separate the liquid, separate the organic phase, the middle of the HPLC of the aqueous phase Body 1 has a purity of 93.87%.

[0072]Put the water phase into a 500ml reaction flask, add 27.20g of ammonium formate and 1.28g of palladium carbon, stir and heat up to 50±5°C, react for 3h, filter off palladium carbon, and the purity of HPLC intermediate 2 of the filtrate is 93.21%.

[0073] Put the filtrate into a 1000ml reaction flask, add 600ml of water, under stirring, adjust the pH to 3 ± 0.5 with concentrated hydrochloric acid, then add 30.94g of 2,4,5-t...

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Abstract

The invention discloses a folic acid synthesis method which comprises the following steps: mixing p-nitrobenzoyl chloride and L-glutamic acid in water, carrying out condensation reaction under the condition that the pH value is 10-11, and separating a water phase in a product obtained by the condensation reaction; carrying out reduction reaction on the water phase, ammonium formate and palladium on carbon, and then removing palladium on carbon to obtain a reduction product; and carrying out cyclization reaction on the reduction product, 2, 4, 5-triamino-6-hydroxypyrimidine sulfate, 1, 1, 3-trichloroacetone and pyrosulfurous acid under the condition that the pH value is 2 to 4.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing folic acid. Background technique [0002] Folic acid is a basic variety of vitamins, a substance necessary for the growth and reproduction of body cells, and plays an important role in the division and growth of cells and the synthesis of nucleic acids, amino acids, and proteins. The lack of folic acid in the human body can lead to abnormal red blood cells, an increase in immature cells, anemia, and decreased white blood cells; the lack of folic acid in pregnant women may lead to low birth weight, cleft lip and palate, and heart defects. [0003] There are many foods containing folic acid, but because the natural folic acid is extremely unstable, it is easily oxidized by ultraviolet light, high temperature, etc., and the bioavailability of folic acid is low, so the human body can not really get much folic acid from food. Human requirements fo...

Claims

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Application Information

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IPC IPC(8): C07D475/04
CPCC07D475/04
Inventor 杨结合王哲廖凯俊黄博
Owner 北京斯利安药业有限公司
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