Ammonia → HCID 86593026, compound

Participants

Reaction Steps

To a stirred solution of (3S,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (4S,5R)-4-[4-(benzyloxy)benzyl]-5-({isobutyl[(4-nitrophenyl)sulfonyl]amino}methyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate. (0.18 g, 0.25 mmol) in 6 mL of a 2M solution of ammonia in methanol was added 0.18 g of palladium (on charcoal, 10% Pd, Degussa type). 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 (7:3) as eluent to provide 81 mg (54%) of the title compound. 1H-NMR (DMSO-d6): δ 0.76 (3H,d), 0.80 (3H,d), 1.19,1.33 (3H,s)*, 1.44, 1.50 (3H,s)*, 1.74 (2H,m), 1.89 (1H,m), 2.49-2.75 (6H,m), 2.89-2.99 (2H,m), 3.19 (1H,m), 3.61 (2H,m), 3.80 (1H,m), 4.07 (1H,m), 4.74 (1H,q), 5.50,5.54 (1H,d)*, 5.94 (2H,s,b), 6.54 (2H,d), 6.64 (2H,d), 6.93,6.99 (2H,d)*, 7.13,7.20 (2H,d)*, 9.20, 9.22 (1H,s)*. MS: 605 (M+).

Provenance & Evidence