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Preparation method of L-N-Boc-high tryptophan methyl ester

A high-tryptophan methyl ester and methyl ester technology, applied in organic chemistry and other fields, can solve the problems of unguaranteed single chirality of the final compound, high cost of raw materials and labor, long reaction steps, etc., to achieve cheap and easy-to-obtain raw materials, Low cost and short reaction steps

Inactive Publication Date: 2013-02-06
SHANGHAI STA PHARMA R&D CO LTD
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Problems solved by technology

[0005] The purpose of the present invention is to provide a preparation method of L-N-Boc-homotryptophan methyl ester, which mainly solves the problems of long reaction steps in existing synthetic methods, high raw material and labor costs, difficult operation, and single-handed preparation of the final compound. technical issues that cannot be guaranteed

Method used

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  • Preparation method of L-N-Boc-high tryptophan methyl ester
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  • Preparation method of L-N-Boc-high tryptophan methyl ester

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preparation example Construction

[0020] Preparation of L-2-pyrrolidone-6-carboxylic acid

[0021]

[0022] Steps:

Embodiment 1

[0023] Example 1 : Add L-2-aminoadipic acid (1.61 g, 10 mmol) to acetic acid (30 mL) and water (5 mL). The resulting mixture was reacted at 80°C for about 12 hours. After the reaction of raw materials was monitored by LC-MS, the reactants were concentrated to obtain L-2-pyrrolidone-6-carboxylic acid (1.21 g, yield: 84.6%), which could be used in the next reaction without purification.

Embodiment 2

[0024] Example 2 : Add L-2-aminoadipic acid (1.61 g, 10 mmol) to acetic acid (30 mL) and water (5 mL). The resulting mixture was reacted at 50°C for about 12 hours. After the reaction of the raw materials was monitored by LC-MS, the reactant was concentrated to obtain L-2-pyrrolidone-6-carboxylic acid (0.20 g, yield: 14.0%), which was used in the next reaction without purification.

[0025] 1 HNMR (DMSO, Bruker Avance 400 MHz):δ 1.623 (m, 2H), 1.749 (t, J=7.2Hz, 1H), 1.902 (dd, J =8.8Hz, J =4.4 Hz, 1H), 2.110 (m, 2H), 3.924 (m, 2H), 7.4(s, 1H).

[0026] Preparation of L-2-pyrrolidone-6-methyl ester

[0027]

[0028] Steps:

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Abstract

The invention discloses a preparation method of L-N-Boc-high tryptophan methyl ester, which can be mainly used for solving the problems that the reaction steps are more, the cost is low, the operation is difficult, and the single chirality of a final compound can not be ensured in an existing synthesizing method. The preparation method comprises the steps of conducting cyclization reaction to generate L-2-pyrrolidone-6-formic acid 1 by taking L-2-amino adipic acid as initial materials under the action of glacial acetic acid and water; 2. conducting an esterification reaction on the compound 1 and trimethyl silicon diazomethane to obtain L-2-pyrrolidone-6-methyl ester 2; 3. protecting N in the compound 2 by using Boc, then conducting the reduction reaction due to the action of a reducing agent, namely lithium triethylborohydride, and reducing carbonyl in the L-2-pyrrolidone-6-methyl ester protected by N-tert-butylcarbazate; and 4. finally synthesizing the high tryptophan methyl ester protected by the L-N-tert-butylcarbazate by two methods: synthesizing classical fisher benzazole in one method, and removing one molecular water by L-2-pyrrolidinol-6-methyl ester and iodoaniline, rearranging, and conducting Heck reaction under the action of a palladium catalyst to obtain the L-N-Boc-high tryptophan methyl ester in the other method.

Description

technical field [0001] The invention relates to a preparation method of homotryptophan methyl ester, in particular to a preparation method of L configuration-N-Boc-homotryptophan methyl ester. Background technique [0002] The preparation method route of existing L configuration-N-Boc-homotryptophan methyl ester is as follows: [0003] [0004] The above synthetic method has long reaction steps, high cost of raw materials and manpower, difficult operation, and single chirality of the final compound cannot be guaranteed. Contents of the invention [0005] The purpose of the present invention is to provide a preparation method of L-N-Boc-homotryptophan methyl ester, which mainly solves the problems of long reaction steps in existing synthetic methods, high raw material and labor costs, difficult operation, and single-handed preparation of the final compound. technical issues that cannot be guaranteed. [0006] The technical scheme is: a preparation method of L-N-Boc-hom...

Claims

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Application Information

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IPC IPC(8): C07D209/20
Inventor 高飞李冀伟吴欣欣周健赵夕龙武翔何振民马汝建
Owner SHANGHAI STA PHARMA R&D CO LTD
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