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L-selenomethionine preparation method

A technology of selenomethionine and hydrochloric acid solution, applied in the field of fine chemical synthesis, can solve the problems of product needing to be split, serious pollution, complicated treatment process, etc., and achieve the effects of mild reaction conditions, single product and simple process

Inactive Publication Date: 2019-03-08
河南希百康健康产业有限公司
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  • Application Information

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Problems solved by technology

The yield of this method is greatly improved, but the disadvantage is that methyl iodide, which is expensive, highly toxic and highly volatile, is used as the alkylation reagent, and the post-purification treatment process is complicated and the product yield is low
[0013] 2) Troels et al. used methionine as the starting material, methylated with methyl iodide, NaHCO 3 Solution hydrolysis, HCl acidification to form a ring, HBr / HAc ring opening, acid-catalyzed esterification to obtain 4-bromo-2-aminobutyric acid methyl ester hydrochloride intermediate, and then introduce methylselenyl, hydrolysis 7-step reaction to obtain the target compound , the total yield is less than 30%
Although the description of the method is simple, the source of dimethyl diselenide and 4-bromo-α-aminobutyrate is not specified, and neither of them is sold as an industrial product, and the preparation process is complicated
[0015] From the above synthetic methods, it is not difficult to see that most of the existing synthetic processes have problems such as serious pollution, high cost, low yield, products need to be split, and it is difficult to realize industrialization.

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preparation example Construction

[0040] The invention provides a kind of preparation method of L-selenomethionine, comprises the following steps:

[0041] A) Carry out nucleophilic substitution reaction between sodium methylselenide and 3,6-bis-(2-chloroethyl)-2,5-diketopiperazine to obtain 3,6-bis-(2-methylselenoethyl) )-2,5-diketopiperazine;

[0042] B) hydrolyzing the 3,6-bis-(2-methylselenoethyl)-2,5-diketopiperazine obtained in the step A) in a hydrochloric acid solution to obtain L-selenomethionine.

[0043]The present invention has no special restrictions on the source of the 3,6-bis-(2-chloroethyl)-2,5-diketopiperazine, preferably according to the synthesis process route in the present invention, with L-aspartic acid The acid is used as the starting material, and it is prepared by esterification, cyclization and reduction, and chlorination in sequence.

[0044] Concrete preparation steps are as follows:

[0045] Esterifying L-aspartic acid and alcohol under the action of a catalyst to obtain an est...

Embodiment 1

[0084] Preparation of L-selenomethionine using 3,6-bis-(2-chloroethyl)-2,5-diketopiperazine:

[0085] 1. Preparation of 3,6-bis-(2-chloroethyl)-2,5-diketopiperazine

[0086] 1) Esterification

[0087] In a round-bottomed flask equipped with an electric stirrer, a water separator, and a reflux condenser, add 66.5 grams of L-aspartic acid, p-TsOH.H 2 O 90 grams, benzyl alcohol 150 mL and 500 mL benzene. Heat and reflux in an oil bath until no water evaporates, stop the reaction, evaporate most of the benzene, after cooling, add 500mL of a 1:1 mixture of diethyl ether and petroleum ether, put it in the refrigerator overnight, white crystals precipitate, filter, and use A 1:1 mixture of ethanol and ether was recrystallized to obtain 202 g of L-aspartate dibenzyl p-toluenesulfonate with a yield of 82.6%.

[0088] Melting point m.p. is 150~152℃, CHC1 3 :CH 3 OH=7:1R f =0.68, specific rotation [α] D 20=+0.9°(C=1,CH 3 OH).

[0089] 2) Cyclization and reduction

[0090] In a...

Embodiment 2

[0104] Preparation of L-selenomethionine using 3,6-bis-(2-chloroethyl)-2,5-diketopiperazine:

[0105] 1. The preparation method of 3,6-bis-(2-chloroethyl)-2,5-diketopiperazine is the same as in Example 1.

[0106] 2. Preparation of L-selenomethionine

[0107] With stirrer, N 2 Add 400mL of methanol and 2.0g of metallic sodium to the three-necked flask of the airway, and after the sodium dissolves, add 4.2g of sodium borohydride, 2 Under protection, 8.3 g of dimethyl diselenide was added dropwise, and after the drop was completed, the reaction was stirred at 58-60°C for 1 hour;

[0108] Then lower the temperature to 50°C, add 9.6 g of 3,6-bis-(2-chloroethyl)-2,5-diketopiperazine, heat and reflux and stir for 3 hours to 3,6-bis-(2-chloroethyl) The reaction of -2,5-diketopiperazine was complete (TLC detection), filtered while it was hot, and the filtrate was placed in the refrigerator overnight, and a white solid was precipitated, filtered with suction, washed with water, and ...

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Abstract

The invention provides an L-selenomethionine preparation method. The L-selenomethionine preparation method comprises the following steps: A), implementing nucleophilic substitution on sodium methyl hydroselenide and 3,6-bi-(2-chloroethyl)-2,5-diketone piperazine to obtain 3,6-bi-(2- methyl selenide ethyl)-2,5-diketone piperazine; B), hydrolyzing the 3,6-bi-(2- methyl selenide ethyl)-2,5-diketone piperazine obtained in the step A) in a hydrochloric acid solution to obtain L-selenomethionine. The 3,6-bi-(2-chloroethyl)-2,5-diketone piperazine is used as a reaction substrate, substitutes, and ishydrolyzed and neutralized with a nucleophilic reagent methyl hydroselenide to obtain the L-selenomethionine, the process is simple, the reaction condition is mild, the product is single, the L-selenomethionine is easy to separate, the yield is high, and the preparation method is suitable of industrial production.

Description

technical field [0001] The invention belongs to the technical field of fine chemical synthesis, and in particular relates to a preparation method of L-selenomethionine. 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 are deficient in selenium to varying degrees. Two-thirds of the regions in my country are ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C391/00
CPCC07C391/00C07D241/08
Inventor 王兴东王小松史苗苗卢会芹
Owner 河南希百康健康产业有限公司
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