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Method for preparing N-substituted-L-methyl tryptophan ester

A technology of tryptophan methyl ester and tryptophan, which is applied in the field of preparation of N-substituted L-tryptophan methyl ester, can solve the problems of long reaction time, unfavorable actual production, high cost, etc., and achieve shortened reaction time and high production efficiency. Effects of cost reduction and utilization efficiency improvement

Inactive Publication Date: 2011-05-11
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Sodium triacetoxyborohydride is an efficient and specific imine reducing agent, but the cost is relatively high, and at the same time, it has the disadvantage of long reaction time, which is not conducive to the actual production requirements

Method used

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  • Method for preparing N-substituted-L-methyl tryptophan ester
  • Method for preparing N-substituted-L-methyl tryptophan ester
  • Method for preparing N-substituted-L-methyl tryptophan ester

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preparation example Construction

[0029] The preparation method of N-substituted L-tryptophan methyl ester of the present invention comprises the following steps:

[0030] 1) Starting from L-tryptophan 1, methylate L-tryptophan methyl ester hydrochloride 2;

[0031] 2) Dehydrochlorination of L-tryptophan methyl ester hydrochloride under alkaline conditions to obtain L-tryptophan methyl ester;

[0032] 3) Condensation reaction of L-tryptophan methyl ester and aromatic aldehyde to obtain imine 3;

[0033] 4) Using sodium borohydride as a reducing agent, the imine is selectively reduced to N-substituted L-tryptophan methyl ester 4.

Embodiment 1

[0036] Step 1: Preparation of L-tryptophan methyl ester hydrochloride:

[0037] Add 50ml of anhydrous methanol to a 100ml three-neck flask, keep the temperature below 0°C in an ice-salt bath, turn on the stirrer, and after the methanol is completely cooled, slowly add 3.27ml of freshly distilled thionyl chloride dropwise with a dropping funnel (45mmol), keep the flow rate as 15 drops per minute, continue to react for 30min after dripping, slowly rise to room temperature and continue to stir for 2h to form solution A; get 6.12g (30mmol) L-tryptophan into solution A, heat up Reflux, and continue to reflux for 5 hours after the L-tryptophan dissolves completely. After the reaction is completed, the solvent methanol and residual thionyl chloride are distilled off under reduced pressure to obtain a white solid, which is finally recrystallized in a mixed solution of methanol and ether. The volume ratio of methanol to diethyl ether was 5:1 to obtain L-tryptophan methyl ester hydrochl...

Embodiment 2

[0051] The step 1, i.e. the preparation method of L-tryptophan methyl ester hydrochloride is the same as in Example 1, so only step 2 is described here, specifically as follows:

[0052] Take 2.03g (8mmol) of L-tryptophan methyl ester hydrochloride and add it to a 100ml three-necked flask, add 20ml of anhydrous methanol and stir until dissolved, add 0.8g (8mmol) of triethylamine under ice-salt bath conditions and continue After stirring for 1 h, a colorless solution was obtained, and then N 2 Drop 8 mmol of anisaldehyde under protection, react below 0°C for 3 hours, then add sodium borohydride in batches, the total amount of sodium borohydride added is 0.363 g (9.6 mmol), continue stirring for 1 hour, and then add water to decompose excess borohydride Sodium and dichloromethane extracted, the organic phase was evaporated to dryness, and the residue was recrystallized with a mixed solvent of chloroform and methanol in an appropriate proportion to obtain the target compound as c...

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Abstract

The invention provides a method for preparing N-substituted-L-methyl tryptophan ester, comprising the following steps: 1) carrying out methyl-esterification on L-tryptophan to obtain L-methyl tryptophan ester hydrochloride; 2) removing hydrochloric acid from the L-methyl tryptophan ester hydrochloride under the alkaline condition to obtain L-methyl tryptophan ester; 3) carrying out a reaction on the L-methyl tryptophan ester and aromatic aldehyde to obtain indole aromatic imine; and 4) reducing the indole aromatic imine into secondary amine by taking sodium borohydride as a reducing agent. The process has the characteristics of cheap and easily obtained raw materials, no need of purification on intermediate products, fast reaction speed, high yield, less environmental pollution, objective economic and practical values and wide application prospect in the pharmaceutical synthesis field, and is simple in reaction operation and easy in final treatment.

Description

technical field [0001] The invention relates to a preparation method of N-substituted L-tryptophan methyl ester. Background technique [0002] N-substituted L-tryptophan methyl ester is a class of secondary amines containing indole structure, and indole compounds belong to an important branch of heterocyclic compounds, are the most widely distributed heterocyclic compounds in nature, and are important organic chemical compounds. Raw materials and products, many compounds containing indole structural units have significant biological activity, and have been widely used in cancer, AIDS, cardiovascular and cerebrovascular diseases, anti-inflammatory, analgesic and other medical fields. As the intermediates of pesticides, spices, dyes and other fine chemical products, compounds with indole structure are more and more widely used. Secondary amines are natural products and synthons of biologically active macromolecules, and are also key active functional groups in modern medicine...

Claims

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Application Information

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IPC IPC(8): C07D209/20C07D405/12
Inventor 马养民刘斌郭满玲徐小娜张弘弛李延超
Owner SHAANXI UNIV OF SCI & TECH
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