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Environmentally-friendly method for synthesizing selenomethionine

An environmentally friendly technology of selenomethionine, applied in the direction of organic chemistry, can solve the problems of low process yield and environmental pollution, achieve high product purity, high process yield, and improve the effect of health and environmental impact

Inactive Publication Date: 2012-07-11
张家港阿拉宁生化技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Sodium methyl selenide (lithium) is obtained by reducing a highly toxic and very foul-smelling dimethyl diselenide. The yield of the whole process is low, which seriously pollutes the environment

Method used

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  • Environmentally-friendly method for synthesizing selenomethionine
  • Environmentally-friendly method for synthesizing selenomethionine
  • Environmentally-friendly method for synthesizing selenomethionine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] The synthesis of embodiment one L-selenomethionine

[0049] Follow the steps:

[0050] one. Synthetic tert-butoxycarbonyl-homoserine (hereinafter referred to as "Boc-HomoSer-OH") belongs to the compound of general formula (2), and its structural formula is as follows:

[0051]

[0052] Dissolve 380g of tert-butoxycarbonyl-L-aspartic acid 4-methyl ester in 3600ml of THF, cool to 0°C with dry ice, add to the reaction kettle, and add NaBH in batches 4 , control the temperature at 5°C to 10°C, and react overnight at 5°C to 20°C after the addition is complete. Add methanol (2000ml) to the reaction solution until no bubbling, stir for ten minutes, concentrate under reduced pressure to remove half of the volume, adjust the pH to 7-8 with 50% phosphoric acid, continue to concentrate the material to dryness to obtain a large amount of viscous, Add 600ml of water, and stir while scraping. After a large amount of viscous matter dissolves, the resulting aqueous layer is extr...

Embodiment 2

[0068] Example 2 Synthesis of D-selenomethionine

[0069] Follow the steps:

[0070] one. Synthesize tert-butoxycarbonyl-D-homoserine, which belongs to the compound of general formula (2), and its structural formula is as follows:

[0071]

[0072] Dissolve 38g of Boc-D-aspartic acid 4-methyl ester in THF (360ml), cool to 0°C with dry ice, add to the reaction kettle, and add NaBH in batches 4 , Control the temperature at 5°C to 10°C. After the addition, react overnight at 5°C to 20°C. Add methanol (200ml) to the reaction solution until it stops bubbling, and stir for ten minutes. After concentrating half of the volume, adjust the pH to 7-8 with 50% phosphoric acid, and continue concentrating to dryness to obtain a large amount of viscous. Add 60ml of water and stir while scraping. After a large amount of viscous matter dissolves, the resulting aqueous layer is extracted with DCM (20 ml each time, repeated 3 times). The ethyl acetate solution obtained by ester extracti...

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Abstract

The invention relates to an environmentally-friendly method for synthesizing selenomethionine. The method comprises the following steps of: reducing alpha-amido-protected aspartate beta-alkyl grease into alpha-amido-protected homoserine, then carrying out acid catalysis for ring closing to obtain inner grease of the homoserine, then reacting with metal selenide to generate homocystine selenide, obtaining the alpha-amido-protected homoserine, and finally eliminating protection and obtaining a selenomethionine product. The environmentally-friendly method has the advantages that the highly-toxic and rotten dimethyl diselenide is prevented from being used, so that the damage to the environment and operators are greatly reduced; the yield is high, the production cost is lower, the product purity is high, and optical and pure selenomethionine can be produced by large batch; and the obtained product can be used for preparing the intermediate of a selenium-containing medicine, and solves the difficulty that the selenomethionine and the related medicines can not be popularized.

Description

technical field [0001] The invention relates to a method for synthesizing selenomethionine as an intermediate of selenium-containing medicines, in particular to an environment-friendly method for synthesizing selenomethionine. Background technique [0002] Selenium is an indispensable trace element for human and animal physiology. Selenium deficiency may cause dysfunction of vital organs in the human body and lead to the occurrence of various diseases. The physiological role of selenium is basically exerted by selenoproteins. A large number of studies have shown that selenium has the following physiological effects: selenium preparations have good preventive and therapeutic effects on coronary insufficiency; selenium can inhibit peroxidation, scavenge harmful free radicals, decompose peroxides and repair molecular damage. Selenium-deficient patients can achieve the effect of assisting in the treatment of asthma by increasing the level of selenium in the body; selenium can ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C391/00
Inventor 向双春夏云超李云平顾小春
Owner 张家港阿拉宁生化技术有限公司
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