HCID 86593024, compound → HCID 86593023, compound

Participants

Reaction Steps

To a stirred solution of (3S,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-{isobutyl[(4-nitrophenyl)sulfonyl]amino}propylcarbamate (0.20 g, 0.29 mmol) in 3 mL of ethanol was added 64 mg of platinum (on activated carbon, 3% Pt). The mixture was stirred under an atmospheric pressure of hydrogen for 12 hours. The catalyst was filtered, and the solvent was removed under reduced pressure. The residue was purified on silica gel using ethyl acetate-hexanes (4:1) as eluent to provide 0.10 g (52%) of the title compound. 1H-NMR (DMSO-d6): δ 0.74 (3H,d), 0.81(3H,d), 1.19 (1H,m), 1.29(1H,m), 1.89 (1H, m), 2.34 (1H,t), 2.54-2.62 (2H,m), 2.71 (1H,m), 2.90 (2H,m), 3.22 (1H,d), 3.46 (1H,m), 3.52-3.59 (3H,m), 3.66 (1H,t) 3.83 (1H,dd), 4.80 (1H,q), 4.92 (1H,d,b), 4.99 (2H,s), 5.47 (1H,d), 5.94 (2H,s), 6.54 (2H,d), 6.81 (2H,d), 7.07(2H,d), 7.19 (1H,d), 7.28 (1H,d), 7.35 (5H,m). MS: 655 (M+).

Provenance & Evidence