Sodium Bicarbonate → HCID 86757974, compound

Participants

Reaction Steps

dl-[5-Cyclohexylmethyl-2-(3-methyl-4-{3-[tert-butoxycarbonyl-(pyridin-3-ylmethyl)-amino]-propoxy}-benzofuran-2-yl)-trans-4,5-dihydro-oxazol-4-yl]-(4-methyl-piperazin-1-yl)-methanone (11.9 mg) was dissolved in 1:1 mixture of trifluoroacetic acid and dichloromethane (1 ml) and was allowed to stand at room temperature for 45 minutes. The resulted solution was poured into saturated aqueous sodium bicarbonate and extracted with dichloromethane. The organic layer was dried over magnesium sulfate and filtered. After evaporation of the solvent the crude product was purified by silica gel column chromatography (Fuji Silysia, DU-3050) using 1000:10:1 mixture of dichloromethane, methanol and triethylamine as an eluent to give the title compound (7.7 mg) as a white solid. FAB-MS: m/z 588 (MH+); NMR (CDCl3): δ 0.9-2.0 (13H, m), 2.06 (2H, quintet, J=6.27 Hz), 2.34 (3H, s), 2.43 (2H, t, J=4.95 Hz), 2.55 (2H, m), 2.62 (3H, s), 2.89 (2H, t, J=6.93 Hz), 3.70 (2H, m), 3.81 (1H, m), 3.84 (2H, s), 4.07 (1H, m), 4.16 (2H, t, J=5.93 Hz), 4.55 (1H, d, J=6.60 Hz), 5.54 (1H, m), 6.61 (1H, d, J=7.92 Hz), 7.10 (1H, d, J=8.25 Hz), 7.15-7.30 (2H, m), 7.67 (1H, dt, J=7.92 Hz, 1.98 Hz), 8.49 (1H, dd, J=1.65 Hz, 4.95 Hz), 8.57 (1H, d, J=1.98 Hz).

Provenance & Evidence