Preparation method of L-selenocystine

A technology for selenocystine and dimethylcystine, which is applied in the field of preparation of L-selenocystine, can solve the problems of difficult separation and purification of substituted products, complicated processes, and tediousness.

Active Publication Date: 2019-02-22
河南希百康健康产业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In the first method, the source of raw materials is difficult, the price is high, the replacement product is difficult to separate and purify, and the yield is low; in the second method, the source of raw materials is difficult, there is no domestic manufacturer, the price is high, the process is complicated, cumbersome, lengthy, and the yield is low. Suitable for laboratory preparation but not for industrial production

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  • Preparation method of L-selenocystine
  • Preparation method of L-selenocystine
  • Preparation method of L-selenocystine

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preparation example Construction

[0027] The invention provides a kind of preparation method of L-selenocystine, comprises the following steps:

[0028] A) carrying out nucleophilic substitution reaction between sodium diselenide and N-acetyl-3-chloro-L-serine methyl ester to obtain N,N'-diacetyl-L-selenocystine dimethyl ester;

[0029] B) Hydrolyzing N,N'-diacetyl-L-selenocystine dimethyl ester in hydrochloric acid solution to obtain L-selenocystine.

[0030] The present invention preferably prepares sodium diselenide according to the following steps, and then performs nucleophilic substitution reaction between sodium diselenide and N-acetyl-3-chloro-L-serine methyl ester to obtain N,N'-diacetyl- L-Selenocystine Dimethyl Ester;

[0031] Under the conditions of ice bath and nitrogen protection, elemental selenium and sodium borohydride are reacted in a solvent to obtain sodium diselenide. The present invention preferably now mixes a part of elemental selenium with a solvent, then adds sodium borohydride unde...

Embodiment 1

[0052] Preparation of L-selenocystine using N-acetyl-3-chloro-L-serine methyl ester:

[0053] Add 30g of selenium powder and 500mL of water into a 2L flask equipped with an electric stirrer, a reflux condenser, and an air guide tube, stir to make it evenly mixed, and then pour N 2 Under protection and ice bath, slowly add 30g of sodium borohydride for about 0.5h, raise to room temperature for 20min, then add 30g of selenium powder, react at room temperature for 20min, rise to 70°C for 20min to obtain a reddish-brown solution ;

[0054] Cool the above solution to about 0°C, add 500mL tetrahydrofuran, stir evenly, add 120g N-acetyl-3-chloro-L-serine methyl ester, continue the reaction for 4h, then raise the temperature to 37°C for 12h until N-acetyl-3- Chloro-L-serine methyl ester was completely reacted (TLC detection), adjusted to pH<5.0 with 6M HCl, extracted three times with ethyl acetate, combined organic phases, washed with water, dried over anhydrous sodium sulfate, filte...

Embodiment 2

[0064] Preparation of L-selenocystine using N-acetyl-3-chloro-L-serine methyl ester:

[0065] Add 30g of selenium powder and 500mL of water into a 2L flask equipped with an electric stirrer, a reflux condenser, and an air guide tube, stir to make it evenly mixed, and then pour N 2 Under protection and ice bath, slowly add 30g of sodium borohydride for about 0.5h, raise to room temperature for 20min, then add 30g of selenium powder, react at room temperature for 20min, rise to 70°C for 20min to obtain a reddish-brown solution ;

[0066] Cool the above solution to about 0°C, add 500mL tetrahydrofuran, stir evenly, add 100g N-acetyl-3-chloro-L-serine methyl ester, continue the reaction for 4h, then raise the temperature to 37°C for 12h until N-acetyl-3- The reaction of chloro-L-serine methyl ester was complete (TLC detection), adjusted the system pH<5.0 with 6M HCl, extracted three times with ethyl acetate, combined the organic phases, washed with water, dried over anhydrous sod...

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Abstract

The invention provides a preparation method of L-selenocystine. The preparation method comprises the following steps: A) carrying out nucleophilic substitution reaction on sodium diselenide and N-acetyl-3-chloro-L-serine methyl ester to obtain N,N'-diacetyl-L-selenocystine dimethyl ester; B) hydrolyzing the N,N'-diacetyl-L-selenocystine dimethyl ester in a hydrochloric acid solution to obtain theL-selenocystine. The preparation method takes an N-acetyl-3-chloro-L-serine methyl ester chiral raw material as a substrate and sodium borohydride as a reducingagent, has the characteristics of easy-to-obtain and cheap raw materials, convenience for operation, moderate reaction conditions, single product, easiness for separation and high yield and the like and is suitable for industrial production. A test result proves that the specific rotatory power of the preparation method provided by the invention can reach that [alpha]D<20> is equal to -29.5 DEG (C 0.5, 0.1 MNaOH) and the highest yield of a product is 80.6 percent.

Description

technical field [0001] The invention belongs to the technical field of organic fine chemical synthesis, and in particular relates to a preparation method of L-selenocystine. Background technique [0002] Selenium is an essential trace element for the human body and an important part of various enzymes in the human body. Once the human body is deficient in selenium, it will directly lead to cardiovascular and cerebrovascular diseases, hypertension, metabolic syndrome, gastrointestinal diseases, diabetes, asthma, Parkinson's The occurrence of more than 40 diseases such as liver disease, liver disease and cancer indirectly leads to the occurrence of more than 400 diseases. Therefore, the great effect of selenium on human health cannot be replaced by other substances. According to the data released by the World Health Organization, there are more than 40 countries and regions in the world that suffer from selenium deficiency in varying degrees. 72% of my country's regions are s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
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
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