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Preparation method of optically pure (-)-clausenamide compound

A technique for the production of pancetamide and its compounds, which is applied in the field of preparation of -bantamide compounds, can solve the problems of restricting the industrial production of optically pure (-)-bantamide, and achieve the environmental protection of the oxidation method, the improvement of efficiency, and the post-treatment easy effect

Inactive Publication Date: 2012-11-14
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Existing methods for preparing optically pure (-)-cantamide require post-processing issues such as chiral resolution or column purification, which limits the industrial production of optically pure (-)-cantamide

Method used

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  • Preparation method of optically pure (-)-clausenamide compound
  • Preparation method of optically pure (-)-clausenamide compound
  • Preparation method of optically pure (-)-clausenamide compound

Examples

Experimental program
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Effect test

Embodiment 1

[0039] The preparation of embodiment 1, (-)-bantamide

[0040] (1) Preparation of (+)-(2S, 3R)-t-butyl epoxy cinnamate

[0041]

[0042] The reaction equation is shown in the above formula, where Ph is phenyl; t-Bu is tert-butyl; Ac is acetyl;

[0043] Add trans-tert-butyl cinnamate (1.0mol, 204.0g) dissolved in 5.0L acetonitrile to a 50L reaction kettle with a mechanical stirrer cleaned with deionized water, and dissolve in 2.5L acetonitrile to obtain the concentration It is a chiral ketone derived from fructose shown in formula (1) of 0.12M (wherein, the molar fraction ratio of tert-butyl cinnamate and chiral ketone derived from fructose shown in formula (1) is 1: 0.30), and Add tetra-n-butylammonium bisulfate (0.06mol, 20.0g), and then add 5.0L of 1×10 -4 The aqueous solution of disodium ethylenediaminetetraacetic acid of M; pass the cooling liquid into the interlayer of the reaction kettle, adjust the temperature in the reaction kettle to be -5°C; add 3.08kg of the pu...

Embodiment 2

[0063] The preparation of embodiment 2, (-)-bantamide

[0064] (1) Preparation of (+)-(2S, 3R)-epoxycinnamic acid ethyl ester

[0065]

[0066] The reaction equation is shown in the above formula, where Ph is phenyl; Ac is acetyl;

[0067] In the 5L reaction kettle with mechanical stirrer that has been cleaned with deionized water, add the trans ethyl cinnamate (0.1mol, 17.62g) that is dissolved in 0.5L acetonitrile, the concentration obtained in being dissolved in 0.25L acetonitrile is The chiral ketone derived from fructose shown in 0.12M formula (1) (wherein, the molar fraction ratio of ethyl cinnamate and the chiral ketone derived from fructose shown in formula (1) is 1: 0.30), and adding four n-Butylammonium bisulfate (0.006mol, 2.0g), then add 0.5L1×10 -4 Aqueous solution of disodium ethylenediaminetetraacetic acid of M; pass cooling liquid into the interlayer of the reaction kettle, adjust the temperature in the reaction kettle to -5°C-5°C; 0.308kg potassium hydro...

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Abstract

The invention discloses a preparation method of a (-)-clausenamide compound shown in formula (I), which comprises the following steps: catalyzing the asymmetric epoxidation reaction of trans-cinnamate by using fructose-derived chiral ketone or chiral ketone hydrate as a catalyst; and then, sequentially carrying out ester exchange reaction, oxidation reaction, cyclization reaction and reduction reaction to finally obtain the optically pure (-)-clausenamide compound shown in formula (I).

Description

technical field [0001] The invention relates to a preparation method of optically pure (-)-bananamide compounds. Background technique [0002] Lansium amide compounds are a class of amide compounds with physiological activity extracted from the leaves, stems and fruits of the folk Chinese herbal medicine Clausena Lansium (Lour) skeels in southern my country. Professor Huang Liang's group at the Institute of Materia Medica, Chinese Academy of Medical Sciences has done a lot of work on the extraction of active ingredients from leaves of wampum, and has achieved very rich research results, and defined the compound with the structure of general formula (a) as pampiamide. So far, people have isolated nearly 20 kinds of amide compounds from wampes. Subsequent studies on the biological activity of these compounds have shown that optically pure (-)-cantamide has obvious effects of promoting intelligence and anti-acute cerebral ischemia, and delaying tissue aging, so it is expected ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/273
CPCC07D207/273
Inventor 史一安彭先友李培军
Owner INST OF CHEM CHINESE ACAD OF SCI
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