A method for preparing a key chiral fragment of artemisinic acid

A key technology of artemisinic acid, which is applied in the field of preparation of a key chiral fragment of artemisinic acid, can solve the problems of asymmetric synthesis of artemisinic acid that have not been reported yet, and achieve a simple route, high yield, and simple operation Effect

Active Publication Date: 2020-01-10
XINJIANG INST OF MATERIA MEDICA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, most of the researches on artemisinic acid focus on its derivatization and further activity testing, and there is no report on the asymmetric synthesis of artemisinic acid.

Method used

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  • A method for preparing a key chiral fragment of artemisinic acid
  • A method for preparing a key chiral fragment of artemisinic acid
  • A method for preparing a key chiral fragment of artemisinic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Synthesis of compound 3(S)-4-benzyl-3-((R)-4-(tert-butyldimethylsilyloxy)-3-methylbutyryl)-2-oxazolidinone:

[0046] Under nitrogen protection, compound 2(R)-4-((tert-butyldimethylsilyl)oxy)-3-methylbutanoic acid (47.5g, 204mmol) was dissolved in 800ml dry tetrahydrofuran (THF ), add triethylamine (56ml, 408mmol) and pivaloyl chloride (30ml, 243mmol) at -78°C, react for 2h, then add lithium chloride (25.9g, 612mmol), (S)-4-benzyl -2-oxazolidinone (36.2g, 204mmol), reacted for 18 hours, then turned off the low-temperature refrigeration, slowly raised the temperature, stirred overnight, quenched the reaction system with water, removed THF by rotary evaporation, then extracted 3 times with ethyl acetate, saturated Washed once with brine, dried over anhydrous magnesium sulfate, filtered, concentrated, and column chromatographed to obtain compound 3(S)-4-benzyl-3-((R)-4-(tert-butyldimethylsiloxane yl)-3-methylbutyryl)-2-oxazolidinone (72.8 g, 92%);

[0047] Synthesis of co...

Embodiment 2

[0071] Synthesis of compound 3(S)-4-benzyl-3-((R)-4-(tert-butyldimethylsilyloxy)-3-methylbutyryl)-2-oxazolidinone:

[0072] Under nitrogen protection, compound 2(R)-4-((tert-butyldimethylsilyl)oxy)-3-methylbutanoic acid (47.5g, 204mmol) was dissolved in 800ml dry tetrahydrofuran (THF ), add triethylamine (56ml, 408mmol) and pivaloyl chloride (30ml, 243mmol) at -78°C, react for 2h, then add zinc chloride (83.4g, 612mmol), (S)-4-benzyl -2-oxazolidinone (36.2g, 204mmol), reacted for 30min, then turned off the low-temperature refrigeration, slowly raised the temperature, stirred overnight, quenched the reaction system with water, removed THF by rotary evaporation, then extracted 3 times with ethyl acetate, saturated salt Washed once with water, dried over anhydrous magnesium sulfate, filtered, concentrated, and column chromatographed to obtain compound 3(S)-4-benzyl-3-((R)-4-(tert-butyldimethylsilyloxy )-3-methylbutyryl)-2-oxazolidinone (72.8 g, 92%);

[0073] Synthesis of compo...

Embodiment 3

[0096] Synthesis of compound 3(S)-4-benzyl-3-((R)-4-(tert-butyldimethylsilyloxy)-3-methylbutyryl)-2-oxazolidinone:

[0097] Under nitrogen protection, compound 2(R)-4-((tert-butyldimethylsilyl)oxy)-3-methylbutanoic acid (47.5g, 204mmol) was dissolved in 800ml dry tetrahydrofuran (THF ), add triethylamine (56ml, 408mmol) and pivaloyl chloride (30ml, 243mmol) at -78°C, react for 2h, then add magnesium chloride (25.9g, 612mmol), (S)-4-benzyl-2 -Zoxazolidinone (36.2g, 204mmol), reacted for 25 hours, then turned off the low-temperature refrigeration, slowly raised the temperature, stirred overnight, quenched the reaction system with water, removed THF by rotary evaporation, then extracted 3 times with ethyl acetate, and saturated saline Wash once, dry over anhydrous magnesium sulfate, filter, concentrate, and column chromatography to obtain compound 3(S)-4-benzyl-3-((R)-4-(tert-butyldimethylsilyloxy) -3-methylbutyryl)-2-oxazolidinone (72.8 g, 92%);

[0098] Synthesis of compound ...

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PUM

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Abstract

The invention discloses a method for preparing a key chiral fragment of rupestonic acid. The method comprises synthesis conversion of an intermediate 2-1, a synthetic method relates to the steps from1 to 10, the existed active researches show that rupestonic acid has obvious biological activity, and especially has good inhibition effect for influenza virus, development of a high-efficiency asymmetric synthesis method of rupestonic acid has important meaning for researching the structure of the rupestonic acid, derivatization is carried out during a synthesis process, and the method has greathelp for discovering novel compounds having better activity. The method has the advantages of simple reaction condition and high selectivity, realizes massive preparation, and establishes a base for asymmetric synthesis of rupestonic acid.

Description

technical field [0001] The invention provides a method for preparing a key chiral fragment of artemisinic acid, which is simple, efficient, good in selectivity, and can be prepared in large quantities. It laid the foundation for the asymmetric synthesis of artemisinic acid. Background technique [0002] Artemisia rupestris L. is the whole herb of Artemisia rupestris L., a plant of the genus Artemisia in the family Compositae. It mainly grows in the Tianshan Mountains, Altai Mountains and Kunlun Mountains in Xinjiang. "Uyghur Medicine Records" records: Artemisia argyi has the effects of dispelling wind and activating blood, dissipating blood stasis and reducing swelling, invigorating stomach and eliminating food, clearing away heat and detoxification, antibacterial, anti-allergic, and detoxifying snakes. It can be used to treat poisonous snake bites, urticaria, indigestion, and colds. , Hepatitis, etc. At present, Xinjiang Yizhihao granules have been approved for marketing ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/18
CPCC07F7/1804C07F7/1892
Inventor 顾政一沙先谊贺金华戎晓娟蔡晓翠
Owner XINJIANG INST OF MATERIA MEDICA
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