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Method of preparing methylselenocysteine from alpha-amino acrylic acid derivative

A technology of α-aminoacrylic acid and selenocysteine, which is applied in the field of amino acid drug preparation, can solve the problems of high production cost, complex process route, and low yield, and achieve the effects of low cost, simple process, and high yield

Active Publication Date: 2009-10-28
江西川奇药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is difficult because of chloroalanine raw material source, and production cost height is unfavorable for large-scale production (Majeed; Muhammed (Piscataway, NJ); Nagabhushanam; Kalyanam (North Brunswick, NJ); Manufacturing processes for Se-methyl-L-selenacysteine, US 6794537B1, 2004)
[0007] Some of the above preparation methods have difficulties in source of raw materials, expensive prices lead to high production costs, some have complicated process routes, pollute the environment, low yield, low product purity, and some have harsh reaction conditions, high equipment requirements and difficult management. Defects, not conducive to mass production, difficult to meet the growing market demand

Method used

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  • Method of preparing methylselenocysteine from alpha-amino acrylic acid derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Preparation of selenomethylselenocysteine ​​using N-acetyl-α-aminoacrylic acid:

[0048] Dissolve 39 grams of N-acetyl-α-aminoacrylic acid in 300 ml of tetrahydrofuran, add 400 ml of water, add solid sodium bicarbonate to saturation, then add 40 grams of solid sodium bicarbonate, then pass through methylselenol at 25 ° C, and seal Keep 2kg / cm 2 Pressure, stirring reaction for 48 hours until N-acetyl-α-aminoacrylic acid reaction is complete (thin-layer chromatography detection); After removing the solid by filtration, use (1+1) hydrochloric acid to neutralize to a pH of about 1, and then use an equal volume of acetic acid Extract with ethyl ester, combine the organic phases and dry with anhydrous sodium sulfate, evaporate the solvent to dryness under reduced pressure to obtain a solid, dissolve it in methanol, remove the insoluble matter by filtration, place the methanol solution, and precipitate a white solid, recrystallize from methanol to obtain N-acetyl - 58 grams o...

Embodiment 2

[0051] Preparation of selenomethylselenocysteine ​​using N-acetyl-α-aminoacrylic acid:

[0052] Dissolve 39 grams of N-acetyl-α-aminoacrylic acid in 300 ml of tetrahydrofuran, add 400 ml of water, add solid sodium bicarbonate to saturation, and then add 40 grams of solid sodium bicarbonate. Methylselenol was introduced at 65°C, and kept sealed at 2kg / cm 2 pressure, stirred and reacted for 40 hours until the reaction of N-acetyl-α-aminoacrylic acid was complete (detected by thin-layer chromatography). After the solid was removed by filtration, it was neutralized with (1+1) hydrochloric acid to a pH of about 1, then extracted with an equal volume of ethyl acetate, the organic phases were combined and dried with anhydrous sodium sulfate, and the solvent was evaporated to dryness under reduced pressure to obtain a solid , dissolved in methanol, filtered to remove insoluble matter, the methanol solution was placed, and a white solid was precipitated, recrystallized from methanol t...

Embodiment 3

[0055] Preparation of selenomethylselenocysteine ​​using N-acetyl-α-aminoacrylic acid:

[0056] Dissolve 39 grams of N-acetyl-α-aminoacrylic acid in 300 ml of tetrahydrofuran, add 400 ml of water, add solid sodium bicarbonate to saturation, and then add 40 grams of solid sodium bicarbonate. Methylselenol was introduced at 100°C, and kept sealed at 10kg / cm 2 pressure, stirring and reacting for 30 hours until the N-acetyl-α-aminoacrylic acid was completely reacted (detected by thin-layer chromatography). After the solid was removed by filtration, it was neutralized with (1+1) hydrochloric acid to a pH of about 1, then extracted with an equal volume of ethyl acetate, the organic phases were combined and dried with anhydrous sodium sulfate, and the solvent was evaporated to dryness under reduced pressure to obtain a solid , dissolved in methanol, filtered to remove insoluble matter, the methanol solution was placed, and a white solid was precipitated, recrystallized from methanol...

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Abstract

The invention discloses a method for synthesizing selenomethylselenocysteine ​​by using alpha aminoacrylic acid derivatives. First, the addition reaction of methylselenol or methylselenol salt solution with α-aminoacrylic acid derivatives generates β-methylselenyl-α-alanine derivatives, and then derivatizes β-methylselenyl-α-alanine The ester compound in the product is hydrolyzed and saponified by sodium bicarbonate, sodium hydroxide or potassium hydroxide, acidified with hydrochloric acid or sulfuric acid to obtain its carboxylic acid compound, and then the N-acyl group is hydrolyzed with hydrochloric acid or sulfuric acid to obtain β-methyl selenium Base-α-alanine hydrochloride or sulfate, and finally neutralized with ammonia or triethylamine to obtain selenomethylselenocysteine. The method has the advantages of simple synthetic route, high yield, environmental protection and low cost, 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 selenomethylselenocysteine ​​by using α-aminoacrylic acid derivatives. Background technique [0002] Selenium is an essential trace element for the human body. Selenium deficiency can lead to diseases such as Keshan disease, Kaschin-Beck disease, heart disease, hypothyroidism and low immune function. Selenium methyl selenocysteine ​​is one of the forms of organic selenium in selenium-rich natural foods. It has the functions of supplementing selenium, preventing cancer, anti-oxidation, anti-aging, treating cardiovascular and cerebrovascular diseases, and detoxifying heavy metals. A stable, efficient and safe selenium supplement ingredient, which is widely used in medicine, nutrition and health care and agriculture. It is of great practical significance to research and develop the preparation method of selenomethylselenocysteine. [0003] The p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C391/00
Inventor 刘建群张小平朱卫丰杨明尹家琪寇晓莉
Owner 江西川奇药业有限公司
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