Ethanol → HCID 56999328, compound

Participants

Reaction Steps

(2S, 3S )-2-Acetoxy-3-[[N-benzyloxycarbonyl-(L )leucyl]amino]tetrahydrofuran (3.2 g) was dissolved in ethanol (150 ml) followed by addition of palladium-on-carbon (5%, 1.5 g) and the catalytic hydrogenation was carried out at ambient temperature and atmospheric pressure. The catalyst was then filtered off and α-naphthyl isocyanate (1.5 g) was added to the filtrate. This mixture was stirred at room temperature for 3 hours. The reaction mixture was then concentrated under reduced pressure to obtain (2S,3S)-2-acetoxy-3-[[N-(1-naphthylcarbamoyl)-(L)-leucyl]amino]-tetrahydrofuran (chemical formula below) (2.95 g, 89%). As recrystallized from dichloromethane-methanolisopropyl ether, colorless crystals, m.p. 196°-198° C., optical rotation [α]D -51.8° (c=0.32, CHCl3). ##STR51##

Provenance & Evidence