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A kind of method adopting one pot method to synthesize selenomethionine

A technology of selenomethionine and diselenide, which is applied in the production of organic chemistry and bulk chemicals, can solve the problems of unfriendly environment, cumbersome operation steps, and difficulty in large-scale production, so as to avoid toxic pollution, high product purity, The effect of reducing pollution

Active Publication Date: 2021-03-23
SUZHOU TOKIND CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] (1) Addition ring-opening method of α-aminobutyrolactone hydrochloride and sodium methylselenol (see Chinese invention patent with application number CN201110152981.8): using α-aminobutyrolactone hydrochloride and methylselenol Addition of sodium opens the ring, and the preparation of sodium methylselenide requires toxic and foul-smelling dimethyl diselenide as raw materials, which is difficult to produce on a large scale
[0004] (2) Homocystine method (see Chinese invention patent with application number CN20121006664.X): that is to use α-amino-protected homoserine lactone to react with metal diselenide to generate α-amino-protected diselenated homocystine acid, and then through reduction and deprotection to obtain selenomethionine. Although this method avoids the use of highly toxic and foul-smelling dimethyl diselenide diselenide, the operation steps are cumbersome
Our extensive research has found that each step of the step-by-step process has a foul-smelling, toxic taste, and uses expensive, volatile, and highly toxic methyl iodide as an alkylating agent in the alkylation step, resulting in a product that is too dark , difficult to purify
[0005] In summary, the existing methods for the preparation of selenomethionine will produce a large amount of toxic and foul-smelling dimethyl diselenide during the preparation process, which is not friendly to the environment, damages the health of operators, or the operation steps are cumbersome and the yield is low, and some The raw material of the step is expensive and dangerous and the operability is not strong

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] A method for synthesizing selenomethionine by a one-pot method is provided, comprising the steps of: weighing 3.95g of selenium powder and adding it to a 250mL four-necked bottle, adding 100mL of THF solution, stirring at room temperature to form a selenium powder suspension, and feeding N 2 , at N 2 Under the protection of the atmosphere, add LiH in batches, heat and stir for 4 hours, then put 12g of benzyloxycarbonyl-L-homoserine lactone into the reaction solution, reflux reaction overnight, let stand and cool down to room temperature, then cool down and stir until the internal temperature reaches - At 25°C, under the protection of nitrogen, add a total of 1.6g of LiH solid to the reaction solution in small amounts; take 7.9g of methyl trifluoromethanesulfonate, dissolve it in 20mL of THF, add it to the reaction solution, and react overnight. Stand still until the internal temperature rises to room temperature; heat and stir, add dropwise 50mL of 1,4-dioxane solution ...

Embodiment 2

[0032] A method for synthesizing selenomethionine by a one-pot method is provided, comprising the steps of: weighing 3.95g of selenium powder and adding it to a 250mL four-necked bottle, adding 100mL of THF solution, stirring at room temperature to form a selenium powder suspension, and feeding N 2 , at N 2 Under the protection of the atmosphere, add LiH in batches, heat and stir for 4 hours; then put 12g of benzyloxycarbonyl-D-homoserine lactone into the reaction solution, reflux reaction overnight, let stand and cool down to room temperature, then cool down and stir until the internal temperature reaches - 25°C; under the protection of nitrogen, add a total of 1.6g of LiH solids to the reaction solution in small amounts several times; take 7.9g of methyl trifluoromethanesulfonate, dissolve it in 20mL of THF, add it to the reaction solution, and react overnight. Stand still until the internal temperature rises to room temperature, heat and stir, add dropwise 50 mL of 1,4-diox...

Embodiment 3

[0034] A method for synthesizing selenomethionine by a one-pot method is provided, comprising the steps of:

[0035] (1) Synthesis of benzyloxycarbonyl-selenohomocysteine, the structural formula is as follows:

[0036] .

[0037] Weigh 3.95g of selenium powder into a 250mL four-neck bottle, add 100mL of THF solution, stir at room temperature to form a selenium powder suspension, and pour N 2 , at N 2 Under the protection of the atmosphere, LiH was added in batches, heated and stirred for 4 hours, and then 12 g of benzyloxycarbonyl-L-homoserine lactone was added to the reaction liquid, and the reaction was refluxed overnight. The resulting reaction solution was rotary evaporated, stirred with water, extracted with EtOAc, and separated, the aqueous phase was adjusted to pH 3~4 with aqueous HCl, extracted with EtOAc, and concentrated to dryness to obtain 15.259 g of yellow oil, yield: 96.77%, HPLC 96.3%.

[0038] (2) Preparation of benzyloxycarbonyl L-selenomethionine, the ...

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PUM

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Abstract

The invention discloses a method for synthesizing selenomethionine by adopting a one-pot method. The method comprises the following steps: mixing selenium and a reducing agent and performing a reducing reaction to obtain metal dioxide M-2Se2; adding alpha-amino protected homoserine lactones in a solution containing metal dioxide M-2Se2 and generated when the reducing reaction is finished to perform a reaction to obtain alpha-amino protected homocysteine diselenide; and reducing the alpha-amino protected homocysteine diselenide, and then performing methylation to obtain alpha-amino protected selenomethionine; and performing deprotection on the alpha-amino protected selenomethionine to obtain selenomethionine. Through the adoption of the way, the method is low in cost, high in yield and highin product purity, can be used for large batch production, avoids toxicity pollution possibly generated in the process link, and greatly reduces environmental pollution and injury to operation personnel.

Description

technical field [0001] The invention relates to the field of medicine and food, in particular to a method for synthesizing selenomethionine by a one-pot method. Background technique [0002] Selenium (Se) is an essential trace element for the human body. Selenium deficiency will cause physiological dysfunction of the human body and lead to the occurrence of Keshan disease and other diseases. Part of the selenium-containing enzymes in the human body can remove peroxides and prevent cell damage. Selenium is also an antioxidant that has a strong antagonistic effect on heavy metals. Therefore, the pharmacological, biological and biochemical properties of selenium cause With people's interest, the development of selenium-containing drugs has become a research hotspot. As a natural organic selenide in living organisms, selenomethionine is gradually replacing traditional inorganic substances such as sodium selenite as a source of selenium supplementation. At the same time, as an i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C391/00
CPCC07C391/00Y02P20/55
Inventor 谢轶能魏开举崔杨
Owner SUZHOU TOKIND CHEM CO LTD
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