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Preparation method of high-optical-purity D- or L-selenomethionine

A technology of selenomethionine and optical purity, which is applied in the direction of organic chemistry, organic chemistry, etc., can solve the problems of unproduct chemical purity and optical purity reporting, inability to meet environmental protection requirements, thiomethyl ether odor, etc., and achieve steps that are easy to operate, The effect of simple steps and simple reaction conditions

Inactive Publication Date: 2017-07-07
安徽至善新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A large number of experiments we conducted found that the yield is very low, which may be related to the alkylation ability of dimethyl sulfate. In addition, the thiomethyl ether produced is too foul to meet the needs of modern large-scale production for environmental protection.
[0031] None of the above methods reported the chemical purity and optical purity of the product

Method used

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  • Preparation method of high-optical-purity D- or L-selenomethionine
  • Preparation method of high-optical-purity D- or L-selenomethionine
  • Preparation method of high-optical-purity D- or L-selenomethionine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Step (1): Under the protection of nitrogen, add 153.30g L-methionine, 250g water, 126.21g methyl chloroformate, 300g acetic acid, and 300mL ethanol into a 1L four-necked flask in sequence. After stirring at room temperature, the temperature is raised to 90°C. After the reaction is complete, the solvent is evaporated.

[0051] Step (2): At low temperature, add 400g of 1,4-dioxane solution with 12% HCl content to the above system, then heat it to reflux for 10h, then cool to room temperature, stir for 2h, vacuum filter, filter The cake is washed with 1,4-dioxane, and the white solid obtained is L-α-amino-γ-butyrolactone hydrochloride, the yield is 79.92%, and the chemical purity is> 99%, optical purity ee> 99%.

[0052] Step (3): Under the protection of nitrogen, mix 13.75 g α-amino-γ-butyrolactone hydrochloride and 40 mL DMF, and stir evenly at room temperature. Dissolve 15.2 g of sodium methyl selenoxide in 20 mL of DMF, add it to the above system, and reflux for 2 hours. ...

Embodiment 2

[0054] Step (1): Under the protection of nitrogen, add 153.10g D-methionine, 420g water, 200mL methanol, and 158.21g diethyl sulfate into a 2L four-necked flask in sequence. After stirring at room temperature, slowly add 45g concentrated sulfuric acid dropwise. After the addition, the temperature was raised to 30-40°C, and after 10 hours, methanol was recovered under reduced pressure. Then adjust the pH of the reaction solution to 8-9 with anhydrous sodium carbonate solid, and continue to react at 40°C for 10 hours. After the reaction is over, the solvent is evaporated under reduced pressure.

[0055] Step (2): Add 260 mL 37% concentrated hydrochloric acid solution to the above system, heat to reflux for 4 hours, evaporate the solvent under reduced pressure to obtain a solid or viscous substance, use hot ethanol to extract the product, and the crude product is subjected to conventional recrystallization treatment Get α-

[0056] Amino-γ-butyrolactone hydrochloride, the yield is 6...

Embodiment 3

[0059] The difference between this embodiment and the first embodiment is that the raw materials used in step (1) are bromoformic acid, chloroformic acid, chloroacetic acid, bromoacetic acid, 1-chloropropionic acid, 1-chlorobutyric acid, methyl chloroacetate, Ethyl chloroformate, ethyl chloroformate, etc. The results are shown in the table below.

[0060]

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Abstract

The invention discloses a preparation method of high-optical-purity D- or L-selenomethionine. The preparation method comprises the following steps: by taking D- or L-methionine as initial raw materials and diethyl sulfate or halogenated alkyl acid or derived esters as alkylation reagents, generating sulfonium salt, desulfurizing and closing ring under acidic conditions, to produce alpha-amino-gama-butyrolactone halate, having addition reaction to alpha-amino-gama-butyrolactone halate with methyl selenol salt and opening ring, acidifying with organic acid, and recrystallizing to obtain D- or L-selenomethionine. The chemical purity of the product is more than or equal to 99%, and the high optical purity is more than or equal to 99%. The preparation method is low-cost and easily available in raw materials, simple in steps and easy to operate, simple in reaction conditions, and suitable for large-scale production.

Description

Technical field [0001] The invention belongs to the technical field of medicine and food, and relates to organic selenium compounds, in particular to a method for preparing D- or L-selenomethionine with high optical purity. Background technique [0002] Selenium is a trace element necessary for life, and it plays an important role in anti-cancer, anti-oxidation, anti-viral diseases, prevention of cardiovascular diseases, cataracts and diabetes. D- or L-selenomethionine is a compound that exists in plants and feed grains in the organic form of selenium in nature. Compared with inorganic selenium, D- or L-selenomethionine has less toxicity and less environmental pollution. The advantages of high bioavailability. However, due to the complex synthesis process and low yield of selenomethionine, there are no reports of industrial production at present, and the price is very expensive. Therefore, the development of a suitable industrial production route of D- or L-selenomethionine is ...

Claims

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Application Information

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IPC IPC(8): C07C391/00
CPCC07C391/00C07B2200/07C07C381/12C07D307/33
Inventor 魏开举任明秀崔杨陈重铭谢轶能
Owner 安徽至善新材料有限公司
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