Synthesis process of theancine

A synthesis method, theanine technology, applied in chemical instruments and methods, preparation of carboxylic acid amides, preparation of organic compounds, etc., can solve the problems of high price, low production cost, and poor selectivity of benzyloxyformyl, and achieve production Low cost, fast response, and high selectivity

Inactive Publication Date: 2005-01-05
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Japanese A.Setsuko et al. (Japanese Patent 278848, 2001) protect the α-amino group of glutamic acid with the Z group (benzyloxyformyl), and mix it with the hydrochloride of ethylamine and triethylamine/sodium carbonate after forming an anhydride Then add it to dimethyl sulfoxide to synthesize N-substituted theanine, remove the protecting group Z group (benzyloxyformyl) by catalytic hydrogenation, and obtain theanine, but the price of the reagent used for the p

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 40 grams of L-glutamic acid and 20 grams of phthalic anhydride into a 500ml flask, control the temperature of the oil bath at 150±5°C, react for 45 minutes after melting, pour it into boiling water while it is hot, cool and crystallize to obtain phthalic acid Acyl L-glutamic acid 32.2 grams (yield 81%) and L-pyroglutamic acid 13.8 grams; Phthaloyl L-glutamic acid 15 grams boiled in acetic acid for 5 minutes to produce phthaloyl L- 12.6 grams of glutamic anhydride (yield 90%); 10 grams of this anhydride is directly reacted with 70% ethylamine aqueous solution at room temperature, because the reaction is more intense, the heat of reaction is released, it is better to slowly add the anhydride or the reaction starts before cooling Carry out under the condition that reacts generally can be finished in ten minutes, distill out ethylamine, concentrate, acidify and can separate out 10.4 grams of phthalyl L-theanines (yield 89%); Dissolve 8 grams of L-theanine directly in 30...

Embodiment 2

[0029] Add 30 grams of L-glutamic acid and 20 grams of phthalic anhydride into a 500ml flask, control the temperature of the oil bath at 150±5°C, react for 50 minutes after melting, pour it into boiling water while it is hot, cool and crystallize to obtain phthalic acid Acyl L-glutamic acid 31.8 grams (yield 80%) and L-pyroglutamic acid 8.1 grams; The following steps are the same as in Example 1.

Embodiment 3

[0031] Synthesize phthalyl-L-theanine with the same operation steps as in Example 1, weigh 10 grams of phthalyl-L-theanine and directly dissolve in 60 ml of 3% hydrazine hydrate at room temperature Put it in the water and ethanol solution for two days, acidify with hydrochloric acid, adjust the pH to 3, filter to remove the precipitate of phthalyl hydrazine, concentrate under reduced pressure, adjust the pH value to 5.5, and crystallize 5.3 grams of crude L-theanine , washed with ethanol and refined to obtain 4.5 grams of refined product.

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Abstract

The invention discloses a theanine synthesizing method, using phthalic anhydride to react with excessive L-glutamic acid at 120-180 deg.C to generate phthalyl L-glutamic acid, which is processed by azeotropism with acetic acid to form phthalyl L-glutamic anhydride, at room temperature, making the phthalyl L-glutamic anhydride directly react with ethylamine water solution to generate phthalyl L-theanine, adding in hydrated hydrazine solution and placing for 2 days to eliminate protective group, so as to obtain L-theanine. And it has the advantages of low price of fast reaction, high selectivity, high yield, generally over 50%, etc.

Description

1. Technical field [0001] The invention relates to a synthesis method of theanine, belonging to the field of chemical synthesis. 2. Technical background [0002] Theanine (L-theanine) is a unique component in tea, and is the free amino acid with the highest content in tea. It has a variety of medicinal and edible functions. Its structural formula is: CH 3 CH 2 NHCOCH 2 CH 2 CH(NH 2 )COOH. According to current literature reports, the chemical synthesis of theanine can be simply summarized into the following three synthetic routes: [0003] The first route: pyroglutamic acid (pyrrolidone acid) method, that is, the reaction of pyroglutamic acid and ethylamine to generate theanine. As early as 1942, Israeli Liechtenstein first used ethylamine and pyrrolidone acid to react in aqueous solution to obtain theanine in the laboratory. In 1951, the Japanese Hashizubin improved the synthesis method, that is, using L-pyrrolidone acid and pure ethylamine to react at low temperature...

Claims

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Application Information

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IPC IPC(8): C07C231/10C07C237/06
CPCY02P20/55
Inventor 焦庆才钱绍松陈然吴晓燕
Owner NANJING UNIV
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