Preparation method of L-Se-methylselenocysteine

A technology of selenocysteine ​​and cysteine ​​methyl ester, applied in organic chemistry methods, organic chemistry and other directions, can solve the problems of difficult source of cysteine ​​raw materials, complex synthesis process, serious pollution, etc.

Active Publication Date: 2019-03-29
河南希百康健康产业有限公司
View PDF7 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] (1) Sodium diselenide method: first react chloroalanine with sodium diselenide to generate selenocystine, then reduce and cleavage the Se-Se bond with metallic sodium/liquid ammonia (-70°C), and then methyl Selenomethylselenocysteine ​​is obtained by chemical reaction. The reaction conditions of this method are harsh, and metal sodium and liquid ammonia are used at ultra-low temperature. Special reaction equipment is required, which is not conducive to large-scale production.
[0009] (2) Sodium methyl selenide method: replace the chlorine in chloroalanine or chloroalanine methyl ester with sodium methyl selenate to obtain selenomethylselenocysteine. This method is due to the raw material source of chloroalanine Difficult, high production cost, low yield, not conducive to large-scale production
In this method, the preparation of the substrate dibromopropionitrile is obtained by addition of acrylonitrile and liquid bromine, but a large amount

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of L-Se-methylselenocysteine
  • Preparation method of L-Se-methylselenocysteine
  • Preparation method of L-Se-methylselenocysteine

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0033] The invention provides a preparation method of L-selenomethylselenocysteine, which comprises the following steps:

[0034] A) Perform a nucleophilic substitution reaction between sodium methylselenoate and N-acetyl-3-chloro-L-serine methyl ester to obtain N-acetyl-3-selenomethyl-L-selenocysteine ​​methyl ester;

[0035] B) Hydrolyzing the N-acetyl-3-selenomethyl-L-selenocysteine ​​methyl ester obtained in step A) in a hydrochloric acid solution to obtain L-selenomethylselenocysteine.

[0036] In the present invention, preferably under the conditions of ice bath and nitrogen protection, dimethyl diselenide, sodium borohydride and activator are mixed in a solvent and reacted to obtain sodium methyl selenoxide; more preferably, dimethyl diselenide The ether and sodium borohydride are dissolved in the solvent, and then under the conditions of ice bath and nitrogen protection, the activator is added dropwise to obtain sodium methylselenoate.

[0037] The reaction equation of this st...

Embodiment 1

[0058] Use N-acetyl-3-chloro-L-serine methyl ester to prepare L-selenomethylselenocysteine:

[0059] Dissolve 60 grams of dimethyl diselenide and 25 grams of sodium borohydride in 600 mL of THF, cool in an ice bath, and 2 Under protection, start stirring, add 120mL of anhydrous methanol dropwise, after about 0.5h, the dripping process, the reaction is violent, a colorless solution is obtained, after continuing to stir for 0.5h, add 600mL of water, after stirring evenly, slowly add 70.0 G N-acetyl-3-chloro-L-serine methyl ester, after the addition, warm to room temperature naturally, and stir for 12h until the reaction of N-acetyl-3-chloro-L-serine methyl ester is complete (TLC detection), use 6.0MHCl Adjust system pH <5.0, extract with ethyl acetate, combine the extracts, wash with water, dry with anhydrous sodium sulfate, filter, and remove ethyl acetate under reduced pressure to obtain a brown-yellow oily liquid, which is N-acetyl-3-selenomethyl-L-selenium The crude product of ...

Embodiment 2

[0069] Use N-acetyl-3-chloro-L-serine methyl ester to prepare L-selenomethylselenocysteine:

[0070] Dissolve 60 grams of dimethyl diselenide and 25 grams of sodium borohydride in 600 mL of THF, cool in an ice bath, and 2 Under protection, start stirring, add 120mL of anhydrous methanol dropwise, after about 0.5h, the dripping process, the reaction is violent, a colorless solution is obtained, after continuing to stir for 0.5h, add 600mL of water, after stirring evenly, slowly add 80.0 Grams of N-acetyl-2-chloro-L-serine methyl ester, after the addition, warm to room temperature naturally, and stir for 24h until the reaction of N-acetyl-3-chloro-L-serine methyl ester is complete (TLC detection), use 6.0MHCl Adjust system pH <5.0, extract with ethyl acetate, combine the extracts, wash with water, dry with anhydrous sodium sulfate, filter, and remove ethyl acetate under reduced pressure to obtain a brown-yellow oily liquid, which is N-acetyl-3-selenomethyl-L-selenium The crude prod...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
Melting pointaaaaaaaaaa
Specific rotationaaaaaaaaaa
Melting pointaaaaaaaaaa
Login to view more

Abstract

The invention provides a preparation method of L-Se-methylselenocysteine. The preparation method comprises the following steps: A) carrying out a nucleophilic substitution reaction on methyl hydroselenide sodium salt with N-acetyl-3-chloro-L-serine methyl ester to obtain N-acetyl-3-selenium methyl-L-selenocysteine methyl ester; and B) hydrolyzing the N-acetyl-3-selenium methyl-L-selenocysteine methyl ester obtained in the step A) in a hydrochloric acid solution to obtain the L-Se-methylselenocysteine. According to the invention, the N-acetyl-3-chloro-L-serine methyl ester is used as a chiral source reagent, and the obtained product is a single optically active substance, so that complex and tedious splitting process can be overcome. The process has the advantages that raw materials are easily available and cheap, operation is convenient, reaction conditions are mild, the product is single, separation is easy, the yield is high, and the method is suitable for industrial production.

Description

Technical field [0001] The invention belongs to the technical field of organic fine chemical synthesis, and particularly relates to a preparation method of L-selenomethylselenocysteine. Background technique [0002] Selenium is an essential trace element for the human body and an important part of various enzymes in the human body. It has many functions such as anti-oxidation, anti-cancer, detoxification, promoting growth, and improving immunity. Once the body lacks selenium, it will directly lead to cardiovascular and cerebrovascular diseases. The occurrence of more than 40 diseases such as, hypertension, metabolic syndrome, gastrointestinal diseases, diabetes, asthma, Parkinson’s disease, liver disease, cancer, etc., which indirectly leads to the occurrence of more than 400 diseases. Therefore, selenium has a great impact on human health. The effect is irreplaceable by other substances. According to the data released by the World Health Organization, there are more than 40 cou...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07C391/00
CPCC07B2200/07C07C391/00
Inventor 王小松卢会芹王兴东史苗苗
Owner 河南希百康健康产业有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap