tert-butyl 1-(3-(3-(3-(benzyloxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-8-yl)propyl)-1H-indole-2-carboxylate → 3-((8-(3-(2-(tert-Butoxycarbonyl)-1H-indol-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

Participants

Reaction Steps

To a solution of tert-butyl 1-(3-(3-(3-(benzyloxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-8-yl)propyl)-1H-indole-2-carboxylate (0.27 g, 0.32 mmol) in MeOH (5 mL), was added 10%/wt palladium on carbon (0.080 g). The reaction mixture was hydrogenated at 50 psi for 48 hours. It was filtered over Celite, and isolated by preparatory thin layer chromatography in 10% methanol in dichloromethane to obtain the title compound (0.060 g, 30%); 1H NMR (DMSO-d6): δ 1.56 (s, 9H), 1.66 (d, 2H, J=14 Hz), 1.95 (t, 2H, J=6.4 Hz), 2.50-2.66 (m, 4H), 2.88 (bs, 4H), 4.59-4.64 (m, 6H), 6.78 (t, 1H, J=7.2 Hz), 6.88 (d, 2H, J=8.4 Hz), 7.10 (t, 1H, J=7.2 Hz), 7.19-7.31 (m, 3H), 7.48-7.54 (m, 2H), 7.67 (t, 2H, J=8.4 Hz), 7.87 (d, 2H, J=6.4 Hz), 8.13 (s, 1H), 12.75 (bs, 1H); MS for C37H42N4O5 m/z 623.16 (M+H)+.

Provenance & Evidence