Process for the preparation of (3r,3as,6ar)-hexahydrofuro...

Details Process for the preparation of (3r,3as,6ar)-hexahydrofuro... Process for the preparation of (3r,3as,6ar)-hexahydrofuro...

C - Chemistry, Metallurgy

07

D

C07D 493/04 (2006.01)

Patent

CA 2549460

The present invention relates to a process for the preparation of (3R,3aS,6aR)~-hexahydrofuro [2,3-b] furan-3-yl (1S,2R)-3-[[(4-aminophenyl) sulfonyl] (isobutyl) amino]-1-benzyl-2-hydroxypropylcarbamate as well as intermediates for use in said process. More in particular the invention relates to processes for the preparation of (3R,3aS,6aR)-hexahydrofuro [2,3-b] furan-3-yl (1S,2R)-3-[[(4-aminophenyl) sulfonyl] (isobutyl) amino]-1-benzyl-2- hydroxypropylcarbamate which make use of 4-amino-N~ ((2R,3S)-3-amino-2-hydroxy- 4-phenylbutyl)-N-(isobutyl)benzene sulfonamide intermediate, and to processes amenable to industrial scaling up. (3R,3aS,6aR)-hexahydrofuro [2,3-b] furan-3- yl (1S,2R)-3-[[(4-aminophenyl) sulfonyl] (isobutyl) amino]-1-benzyl-2- hydroxypropylcarbamate is particularly useful as HIV protease inhibitors.

L'invention concerne un procédé pour préparer du (3R,3aS,6aR)-hexahydrofuro [2,3-b] furane-3-yle (1S,2R)-3-[[(4-aminophényle) sulfonyle] (isobutyle) amino]-1-benzyle-2-hydroxypropylcarbamate, ainsi que des produits intermédiaires utilisés dans ce procédé. L'invention concerne en particulier des procédés pour préparer du (3R,3aS,6aR)-hexahydrofuro [2,3-b] furane-3-yle (1S,2R)-3-[[(4-aminophényle) sulfonyle] (isobutyle) amino]-1-benzyle-2-hydroxypropylcarbamate, selon lesquels on utilise un produit intermédiaire sulfonamide 4-amino-N- ((2R,3S)-3-amino-2-hydroxy-4-phénylbutyle)-N-(isobutyle)benzène, ainsi que des procédés aptes à l'augmentation à l'échelle industrielle. Le (3R,3aS,6aR)-hexahydrofuro [2,3-b] furane-3-yle (1S,2R)-3-[[(4-aminophényle) sulfonyle] (isobutyle) amino]-1-benzyle-2-hydroxypropylcarbamate est particulièrement utile comme inhibiteur de protéase HIV.

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