HCID 67160330, compound → HCID 45107957, compound

Participants

Reaction Steps

A solution of {[(4aS,13aR)-8-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-9,11-dioxo-2,3,4a,5,9,11,13,13a-octahydro-1H-pyrido[1,2-a]pyrrolo[1′,2′:3,4]imidazo[1,2-d]pyrazin-10-yl]oxy}methyl 3-[(phenylmethyl)oxy]propyl carbonate (2.30 g, 3.52 mmol) in 50 mL of 1:1 MeOH/AcOH was subjected to hydrogenation at 55 psi in the presence of 0.75 g of 10% palladium on charcoal. After 5 hours the reaction vessel was purged with nitrogen, catalyst removed by filtration through celite and the filtrate concentrated to dryness at reduced pressure. The residue was dissolved in dichloromethane and the solution mixed with saturated aqueous sodium bicarbonate. The mixture was stirred vigorously for 25 minutes and the phases separated. The aqueous phase was extracted with one additional portion of dichloromethane. The combined dichloromethane solutions were washed with saturated aqueous brine, dried over sodium sulfate and concentrated to dryness at reduced pressure to give the title compound (1.96 g, 99%) as a light tan foam. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.18 (t, J=5.8 Hz, 1 H), 8.39 (s, 1 H), 7.37-7.26 (m, 1 H), 6.84-6.72 (m, 2 H), 5.93 (d, J=6.6 Hz, 1 H), 5.85 (d, J=6.6 Hz, 1 H), 4.66-4.36 (m, 4 H), 4.34-4.10 (m, 3 H), 3.87 (t, J=11.3 Hz, 1 H), 3.79-3.64 (m, 3 H), 3.17-3.02 (m, 2 H), 2.90-2.74 (m, 2 H), 2.11-1.81 (m, 4 H), 1.71-1.57 (m, 2 H): ES+ MS: 563 (M+1).

Provenance & Evidence