Process for preparing zanamivir and intermediates for use in...

C - Chemistry – Metallurgy – 07 – D

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C07D 309/28 (2006.01)

Patent

CA 2744793

The present invention provides a process for preparing methyl 5-acetamido-4-amino-6- (1,2,3--triacetoxypropyl)-5,6-dihydro-4H-pyran-2- carboxylate (V), which process comprises reducing methyl 5-acetamido-4-azido-6--(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2- carboxylate (IV) in the presence of a reducing agent selected from the group consisting of lithium aluminium hydride, sodium borohydride, zinc/ammonium chloride, zinc-ferric chloride and ferric chloride/sodium iodide. The present invention also provides compounds of formula (VIII) and (IX) which may be used in the syn-thesis of zanamivir. The present invention also provides processes for preparing compounds (VIII) and (IX) and processes involv-ing their use, including in the synthesis of zanamivir.

La présente invention concerne un procédé de synthèse du 5-acétamido-4-amino-6-(1,2,3-triacétoxypropyl)-5,6-dihydro-4H-pyrane-2-carboxylate de méthyle (V), ledit procédé comprenant la réduction du 5-acétamido-4-azido-6-(1,2,3-triacétoxypropyl)-5,6-dihydro-4H-pyrane-2-carboxylate de méthyle (IV) en présence d'un agent réducteur choisi dans le groupe constitué par le lithium aluminium hydrure, le borohydrure de sodium, le zinc/chlorure d'ammonium, le zinc-chlorure ferrique et le chlorure ferrique/iodure de sodium. La présente invention concerne également des composés de formule (VIII) et (IX) pouvant être employés dans la synthèse du zanamivir. La présente invention concerne également des procédés de synthèse des composés (VIII) et (IX) et des procédés impliquant leur utilisation, y compris dans la synthèse du zanamivir.

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