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Process for preparing optics pure abacavir

An optical and synthetic method technology, applied in the field of preparation of optically pure abacavir, can solve the problems of complicated operation, three wastes, etc., and achieve the effect of simple operation and environmental protection

Active Publication Date: 2006-11-15
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The above-mentioned methods all have disadvantages such as complex operation and large amount of three wastes. Therefore, it is necessary to develop a milder and more environmentally friendly method

Method used

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  • Process for preparing optics pure abacavir
  • Process for preparing optics pure abacavir
  • Process for preparing optics pure abacavir

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1 (1S, 4R)-4-[(2,5-diamino-6-chloro-4-pyrimidinyl) amino]-2-cyclopentenyl-1-methanol synthesis

[0025] (1S,4R)-4-amino-2-cyclopentenyl-1-methanol (113mg, 1mmol), 2,5-diamino-4,6-dichloropyrimidine (358mg, 2mmol), 1mL triethylamine , 10mL of methanol, heated to reflux, followed by spotting the plate until the end of the reaction, evaporated the solvent, and separated on a silica gel column to obtain a white flaky solid (1S, 4R)-4-[(2,5-diamino-6-chloro-4-pyrimidine Base)amino]-2-cyclopentenyl-1-methanol 109 mg, yield 43%.

Embodiment 2

[0026] Embodiment 2 (1S, 4R)-4-[(2,5-diamino-6-chloro-4-pyrimidinyl) amino]-2-cyclopentenyl-1-methanol synthesis

[0027] (1S,4R)-4-amino-2-cyclopentenyl-1-methanol (226mg, 2mmol), 2,5-diamino-4,6-dichloropyrimidine (179mg, 1mmol), 2mL triethylamine , 10mL of N,N-dimethylformamide, heated to reflux, followed by spotting the plate until the end of the reaction, evaporated the solvent, and separated on a silica gel column to obtain a white flaky solid (1S,4R)-4-[(2,5-diamino -6-Chloro-4-pyrimidinyl)amino]-2-cyclopentenyl-1-methanol 144 mg, yield 57%.

Embodiment 3

[0028] Embodiment 3 (1S, 4R)-4-[(2,5-diamino-6-chloro-4-pyrimidinyl) amino]-2-cyclopentenyl-1-methanol synthesis

[0029] (1S,4R)-4-amino-2-cyclopentenyl-1-methanol (113mg, 1mmol), 2,5-diamino-4,6-dichloropyrimidine (179mg, 1mmol), 1mL triethylamine , 10mL of dichloromethane, heated to reflux, followed by spotting the plate until the end of the reaction, evaporated the solvent, and separated on a silica gel column to obtain a white flaky solid (1S, 4R)-4-[(2,5-diamino-6-chloro-4 -pyrimidinyl)amino]-2-cyclopentenyl-1-methanol 71 mg, yield 28%.

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Abstract

A process for preparing the optical-purity (99.9% ee) Abakawei features that its initial raw materials are (1S,4R)-4-amino-2-cyclopentyl-1-methanol and 2,5-diamino- 4,6-dichloropyrimidine.

Description

technical field [0001] The present invention relates to a preparation method of optically pure abacavir, namely (1S, 4R)-4-(2-amino-6-cyclopropylamino-9-hydrogen-9-purinyl)-2-cyclopentyl Process for the preparation of alkenyl-1-methanol. Background technique [0002] AIDS (Acquired Immunodeficiency Syndrome, referred to as AIDS) is an infectious disease caused by Human Immunodeficiency Virus (Human Immunodeficiency Virus, referred to as HIV). Spread through sexual contact and blood transfusion. At present, AIDS (AIDS) is widely prevalent in the world, has attracted great attention from governments and relevant international organizations, and has become a major public health and social problem that has attracted worldwide attention. [0003] Since Zidovudine (AZT), the first drug for the treatment of HIV infection / AIDS, was approved by the US FDA in 1987, the research and development of anti-AIDS drugs has advanced by leaps and bounds. At present, more than a dozen drugs h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D473/16
Inventor 姜标赵小龙王万军
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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