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Process for the preparation of cyclopropane derivatives

一种烷基、化合物的技术，应用在环丙烷衍生物的制备领域，能够解决费时保护和去保护步骤、低稳定性中间体、危险产物等问题

Active Publication Date: 2017-11-03
阿拉塔纳医疗股份有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The methods described above suffer from certain disadvantages: synthetic routes include multiple time-consuming protection and deprotection steps, require the use of hazardous products, and / or involve the use of intermediates with low stability

Method used

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  • Process for the preparation of cyclopropane derivatives
  • Process for the preparation of cyclopropane derivatives
  • Process for the preparation of cyclopropane derivatives

Examples

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Embodiment

[0226] The following examples are provided for the purpose of illustrating the invention but are in no way intended and should in no way be construed as limiting the scope of the invention.

[0227] 1) Preparation of (1R, 2R)-1,2-two (hydroxymethyl) ethyl cyclopropanecarboxylate (2c)

[0228]

[0229] In the reactor, ethanol (82.4 L) was added followed by ethyl (1S,5R)-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate (10.3kg, 64.6mol) and cooled to 10°C. Sodium borohydride (1.85 kg, 51.7 mol) was added in portions over a period of 1 hour by maintaining the reaction temperature between 10-15°C. The reaction temperature was raised to 20-25°C and maintained for 1 hour. The progress of the reaction was monitored by HPLC. After the reaction was complete, the reaction mass was cooled to 0-5°C. The pH of the reaction mass was adjusted to 7.0 using 1.5N aqueous HCl at 0-5°C during 1 hour. Ethyl acetate (34.0 L) was added to the reaction mass and the solid was filtered. The clear...

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Abstract

The present invention relates to cyclopropane derivatives, especially 2-amino-9-[[(1S,2R)-1,2-di(hydroxymethyl)cyclopropyl]methyl]-1,9-dihydro-6H- Purin-6-one, especially via the [(1S,7R)-4-phenyl-3,5-dioxabicyclo[5.1.0]octane-1-yl]methanol intermediate.

Description

field of invention [0001] The present invention relates to the preparation of cyclopropane derivatives and to intermediates obtained in said preparation. Background of the invention [0002] Known cyclopropane derivatives such as 2-amino-9-[[(1S,2R)-1,2-bis(hydroxymethyl)cyclopropyl]methyl]-1,9-dihydro-6H-purine- 6-keto has potent antiviral activity. [0003] For the preparation of 2-amino-9-[[(1S,2R)-1,2-bis(hydroxymethyl)cyclopropyl]methyl]-1,9-dihydro-6H-purin-6-one A first method is disclosed in patent EP0502690. The reaction sequence disclosed in these documents involves the preparation of (1S,5R)-2-oxo-3-oxabicyclo[3.1. 0] Ethyl hexane-1-carboxylate. Subsequent conversion to (1S,2R)-1,2-bis(benzoyloxymethyl)cyclopropylmethyl-p-toluenesulfonate requires 8 additional steps including multiple protection and deprotection steps . (1S,2R)-1,2-Bis(benzoyloxymethyl)cyclopropylmethyl-p-toluenesulfonate was then coupled with 2-amino-6-benzyloxy-purine. Finally, removal of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D321/10
CPCC07D239/50C07D321/10C07D473/18C07D473/40
Inventor 埃莱奥诺拉·基斯埃尔温·布洛姆萨塞尔日·德布吕因E·J·N·雷米·里特延斯
Owner 阿拉塔纳医疗股份有限公司
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