Process for the preparation of (2r, 3s)-3-amino-1,2-oxirane

Details Process for the preparation of (2r, 3s)-3-amino-1,2-oxirane Process for the preparation of (2r, 3s)-3-amino-1,2-oxirane

C - Chemistry, Metallurgy

07

D

C07D 301/02 (2006.01) C07D 303/36 (2006.01)

Patent

CA 2306741

A process for the preparation of (2R, 3S)-3-amino-4-phenylbutane-1,2-epoxide, which comprises treating a (2S, 3S)-3-amino-1-halo-2-hydroxy-4-phenylbutane or (2S, 3S)-3-amino-4-phenylbutane-1,2-epoxide either with a quaternary ammonium carboxylate or with both a metal carboxylate and a quaternary ammonium salt to prepare a (2S, 3S)-1-acyloxy-3-amino-2-hydroxy-4-phenylbutane, treating this compound with a sulfonyl halide in the presence of an organic base to prepare a (2S, 3S)-1-acyloxy-3-amino-2-sulfonyloxy-4-phenylbutane, and subjecting the compound thus obtained to treatment with an inorganic base. This process makes it possible to efficiently produce intermediates for HIV protease inhibitors by using L-phenylalanine as a raw material.

L'invention concerne un procédé de préparation de (2R, 3S)-3-amino-4-phénylbutane-1,2-époxyde, qui consiste à traiter un (2S, 3S)-3-amino-1-halo-2-hydroxy-4-phénylbutane ou (2S, 3S)-3-amino-4-phénylbutane-1,2-époxyde, soit au moyen d'un carboxylate d'ammonium quaternaire, soit au moyen d'un carboxylate de métal et d'un sel d'ammonium quaternaire, de sorte qu'un (2S, 3S)-1-acyloxy-3-amino-2-hydroxy-4-phénylbutane soit produit; à traiter ledit composé à l'aide d'halogénure de sulfonyle, en présence d'une base organique, de manière qu'un (2S, 3S)-1-acyloxy-3-amino-2-sulfonyloxy-4-phénylbutane soit produit, et à soumette le composé ainsi obtenu à un traitement à l'aide d'une base inorganique. Ledit procédé permet la production efficace d'intermédiaires pour les inhibiteurs de la protéase de VIH au moyen de L-phénylalanine en tant que matière première.

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