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A method for preparing optically pure L-type selenium-methylselenocysteine

A technology of methylselenocysteine ​​and L-type, which is applied in the field of amino acid drug preparation, can solve the problems of difficult availability of reagents, high price and high cost of chloroalanine

Active Publication Date: 2020-10-27
济源希健生物医药科技发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, existing direct chemical synthesis methods have problems such as difficult acquisition of reagents, high prices, harsh reaction conditions, and long reaction times, such as the synthetic method of sodium chloroalanine diselenide (J.Med.Chem.1996,39,2040- 2046), it needs to be carried out under the condition of -70°C, which requires strict equipment and is difficult to put into large-scale production; for example, the synthetic method of tert-butoxyacyl-protected serine (European patent EP1205471A1, 2001), the reaction time is longer, And the price of the raw material and protective agent involved is higher; such as the synthetic method of sodium methylselenide replacing chloroalanine (U.S. Patent US6794537B1, 2004), the cost of chloroalanine used is high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1 Direct preparation of optically pure L-type selenium-methylselenocysteine ​​by using N-acetyl-3-chloro-L-serine methyl ester

[0041] (1) Under stirring conditions, mix sodium methylselenide, N-acetyl-3-chloro-L-serine methyl ester and anhydrous methanol, and react at -15°C for 2 hours, wherein sodium methylselenide and N-acetyl The molar equivalent ratio of 3-chloro-L-serine methyl ester is 1:1; then adopt the stepwise heating method, stir the reaction at 25°C for 1 hour, stir the reaction at 40°C for 1 hour, and stir the reaction at 65°C for 1 hour. After the reaction is completed, the temperature of the reaction system Cool to -15°C, slowly adjust the pH of the reaction system to 7 with 2mol / L hydrochloric acid solution, extract 3 times with ethyl acetate, combine the extracts, wash with water until neutral, dry the organic phase with anhydrous sodium sulfate, filter, and remove under reduced pressure Ethyl acetate was used to obtain 315 g of N-acetyl-3-met...

Embodiment 2

[0045] Example 2 Using N-acetyl-3-chloro-L-serine methyl ester to directly prepare optically pure L-type selenium-methylselenocysteine

[0046] (1) Under stirring conditions, mix sodium methylselenide, N-acetyl-3-chloro-L-serine methyl ester and anhydrous ethanol, and react at 15°C for 5h, wherein, sodium methylselenide and N-acetyl - The molar equivalent ratio of 3-chloro-L-serine methyl ester is 2:1; then adopt the stepwise heating method, stir the reaction at 40°C for 3 hours, stir the reaction at 65°C for 3 hours, stir the reaction at 75°C for 3 hours, and cool down the reaction system after the reaction is completed to 25°C, slowly adjust the pH of the reaction system to 6 with 6mol / L hydrochloric acid solution, extract 5 times with ethyl acetate, combine the extracts, wash with water until neutral, dry the organic phase with anhydrous sodium sulfate, filter, and remove ethyl acetate under reduced pressure ester to obtain 400 g of N-acetyl-3-methylselenoyl-L-serine methyl...

Embodiment 3

[0049] Example 3 Using N-acetyl-3-chloro-L-serine methyl ester to directly prepare optically pure L-type selenium-methylselenocysteine

[0050] (1) Under stirring conditions, mix sodium methylselenide, N-acetyl-3-chloro-L-serine methyl ester and anhydrous solvent tetrahydrofuran, and react at 0°C for 3 hours, wherein sodium methylselenide and N-acetyl - The molar equivalent ratio of 3-chloro-L-serine methyl ester is 3:1; then adopt the stepwise heating method, stir the reaction at 30°C for 2 hours, stir the reaction at 45°C for 2 hours, stir the reaction at 70°C for 2 hours, and cool down the reaction system after the reaction is completed to 0°C, use 4mol / L hydrochloric acid solution to slowly adjust the pH of the reaction system to 5, extract 4 times with ethyl acetate, combine the extracts, wash with water until neutral, dry the organic phase with anhydrous sodium sulfate, filter, and remove acetic acid under reduced pressure ethyl ester to obtain 350 g of N-acetyl-3-methyl...

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Abstract

The invention relates to a method for preparing an amino acid drug, and in particular to a method for preparing optically pure L-type selenium-methyl selenocysteine. The method comprises the steps ofmixing N-acetyl-3-chloro-L-serine methyl ester with methylselenol salt to obtain N-acetyl-3-methyl selenyl-L-serine methyl ester; mixing with a hydrochloric acid solution and carrying out hydrolysis reaction to obtain selenium-methyl selenocysteine; dissolving the selenium-methyl selenocysteine in water, adding a solvent A and uniformly mixing; adding activated carbon to decolorize, filtering andcollecting filtrate; and adding a solvent B into filtrate, uniformly mixing, cooling, standing for more than 1 hour and collecting crystals to obtain the optically pure L-type selenium-methyl selenocysteine. The method disclosed by the invention has the characteristics of being simple in process, high in product optical purity, green and friendly to environment and is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a method for preparing amino acid medicine, in particular to a method for preparing optically pure L-type selenium-methylselenocysteine. Background technique [0002] Natural selenium-methylselenocysteine ​​is an L-type selenium-containing amino acid, which is the methylated derivative of the 21st essential amino acid for the human body - selenocysteine. It was first isolated from American Astragalus in 1960, and it also widely exists in plants such as garlic, onion and broccoli, as well as selenium-enriched yeast. L-type selenium-methylselenocysteine ​​has the functions of supplementing selenium, preventing and treating cancer, anti-oxidation, anti-aging, treating cardiovascular and cerebrovascular diseases, and detoxifying heavy metals. widespread attention. In 2002, it was recognized by the US FDA as the latest generation of selenium source dietary supplements. In 2009, it was approved by the Ministry of Health of my coun...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C391/00
CPCC07B2200/07C07C391/00
Inventor 姚一姚永强姚品李金冯书晓
Owner 济源希健生物医药科技发展有限公司
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