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Preparation method of levo-5-hydroxytryptophan

A technology of hydroxytryptophan and tryptophan methyl ester, which is applied in organic chemistry and other fields, and can solve the problem that the plant extraction process is affected by seasons, etc.

Active Publication Date: 2012-02-15
FOSHAN PRIZEN MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] In order to solve the deficiencies of the above-mentioned prior art, especially the problem that the plant extraction process is affected by seasons, the object of the present invention is to provide a method with simple reaction operation, easy access to raw materials, easy industrialization, easy post-treatment, high yield, and low environmental pollution. , the preparation method of L-5-hydroxytryptophan

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preparation example Construction

[0036] The preparation method of L-5-hydroxytryptophan of the present invention comprises the following steps:

[0037] 1) Starting from L-tryptophan (1), esterify methyl / ethyl to obtain L-tryptophan methyl / ethyl hydrochloride (2);

[0038] 2) Dehydrochloride L-tryptophan methyl ester / ethyl ester hydrochloride under alkaline conditions to obtain L-tryptophan methyl ester / ethyl ester, and then acetylate it into N-acetyl-L-tryptophan methyl ester / ethyl ester (3);

[0039] 3) Reducing the indole ring with N-acetyl-L-tryptophan methyl / ethyl ester in a triethylsilane-trifluoroacetic acid reduction system to obtain compound (4);

[0040] 4) Compound (4) was oxidized in the 1-position nitrogen of the indole ring under sodium tungstate-30% hydrogen peroxide system to obtain compound (5);

[0041] 5) Compound (5) transfers the hydroxyl group on the 1-position nitrogen of the indole ring to the 5-position carbon of the benzene ring under acidic conditions, and deacetylates to obtain ...

Embodiment 1

[0043] Step 1: Preparation of L-tryptophan methyl ester hydrochloride (2):

[0044] Weigh 174g of L-tryptophan (1) in 1.6L of methanol, cool to 0°C, add 87mL of thionyl chloride dropwise at 0°C, after the dropwise addition, raise the temperature to 30°C and react for 6 hours. After the reaction was completed, the solvent was distilled off under reduced pressure to obtain a white solid. The solid was washed with 300 mL of ether to obtain L-tryptophan methyl ester hydrochloride, which weighed 214 g.

[0045] The characterization parameters of this L-tryptophan methyl ester hydrochloride are as follows:

[0046] Melting point: 232~233℃;

[0047] Mass spectral data: C 12 h 15 ClN 2 o 2 ,[M+H] + = 255.1;

[0048] NMR data:1 H NMR (δ, ppm, DMSO-d6, 400MHz): 3.39 (2H, m, CH 2 ); 3.63 (3H, s, CH 3 O); 4.20 (1H, t, CH, J = 5.5Hz); 7.07 (2H, dt, J = 21Hz, 6Hz); 7.26 (1H, d, J = 3Hz); 7.39 (1H, d, J = 7.8 Hz).

[0049] Step 2: Preparation of N-acetyl-L-tryptophan methyl ester...

Embodiment 2

[0076] Step 1: Preparation of L-tryptophan ethyl ester hydrochloride (2):

[0077] Weigh 174g of L-tryptophan (1) in 1.6L of ethanol, cool to 0°C, add 140mL of thionyl chloride dropwise at 2°C, after the dropwise addition, raise the temperature to 45°C and react for 4 hours. After the reaction was completed, the solvent was distilled off under reduced pressure to obtain a white solid. The solid was washed with 200 mL of diethyl ether to obtain L-tryptophan ethyl ester hydrochloride, which weighed 217.5 g.

[0078] The characterization parameters of this L-tryptophan ethyl ester hydrochloride are as follows:

[0079] Mass spectral data: C 13 h 17 ClN 2 o 2 ,[M+H] + = 269.1;

[0080] NMR data: 1 H NMR (δ, ppm, DMSO-d6, 400MHz): 1.30 (3H, t, CH 3 ); 3.39 (2H, m, CH 2 ); 4.23 (2H, CH 3 O); 4.20 (1H, t, CH, J = 5.5Hz); 7.07 (2H, dt, J = 21Hz, 6Hz); 7.26 (1H, d, J = 3Hz); 7.39 (1H, d, J = 7.8 Hz).

[0081] Step 2: Preparation of N-acetyl-L-tryptophan ethyl ester (3):

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Abstract

The invention provides a preparation method of levo-5-hydroxytryptophan. The method comprises the following steps: performing methyl esterification / ethyl esterification on L-tryptophan to obtain L-tryptophan methyl / ethyl ester hydrochloride, performing dehydrochlorination under the alkaline condition to obtain L-tryptophan methyl / ethyl ester, performing acetylation to obtain N-acetyl-L-tryptophanmethyl / ethyl ester, reducing an indole ring under a triethylsilane-trifluoroacetic acid reduction system, oxidizing 1-position nitrogen of the indole ring under a sodium tungstate-30% hydrogen peroxide system, finally removing acetyl protection group to obtain levo-5-hydroxytryptophan under the acidic condition, further cooling and crystallizing, then enabling mother liquor to pass through a macroporous adsorption resin column, performing concentration, cooling and crystallization, and combining obtained levo-5-hydroxytryptophan crystals. The process has the advantages of being low in price of raw materials, being easy to obtain the raw materials, being simple in reaction operation, being high in yield, being good in product quality, being low in environmental pollution and the like, and is suitable for industrial large-scale production, the purity of the obtained product can achieve 99.2%, and the total yield is above 45%.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a preparation method of L-5-hydroxytryptophan, in particular to a fine chemical method for preparing L-5-hydroxytryptophan by using L-tryptophan as a raw material. Background technique [0002] L-5-hydroxytryptophan (also known as 5-hydroxytryptophan, 5-HTP for short) is a natural plant extract with a molecular weight of 220.23 and has a variety of biological activities. It has been used as an important neurological drug and Health products. [0003] At present, there are three main production methods of 5-HTP. The first one is to extract from leguminous plants, especially Griffonia Simplicifolia, which is native to Africa. For example, the patent CN101648900 reports that Ghana seeds produced in Africa are used as raw materials for supercritical extraction. After degreasing, the material is extracted 3 to 5 times with a mixed solution of water and alcohol solvents, and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/20
Inventor 胡文辉唐星兰小兵余加进
Owner FOSHAN PRIZEN MEDICAL TECH
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