Trifluoroacetic acid → HCID 86597377, compound

Participants

Reaction Steps

A solution of TFA (5 mL) in methylene chloride (10 mL) was added dropwise to the cold (ice bath) solution of tert-butyl (2Z)-3-(3-benzyl-2-ethyl-1-benzofuran-6-yl)pent-2-enyl[(tert-butoxycarbonyl)oxy]carbamate (4.0 g; 7.45 mmol) in methylene chloride (25 mL). The mixture was stirred at ° C. for 1 hour and at room temperature for 1 hour and solvent evaporated. The residue was extracted with ethyl acetate, washed with sodium bicarbonate solution, water, and evaporated to dryness. The residue was chromatographed on silica gel using 2% ethyl acetate in hexane as an eluent to give the title compound (1.8 g) as an oil. 1HNMR (400 MHz, DMSO-d6): δ 0.85 (t, 2H, J=7.25 Hz), 1.05 (t, 3H, J=7.47 Hz), 1.2-1.25 (m, 6H), 2.35 (q, 2H, J=7.47 Hz), 2.85 (q, 3H, J=7.47 Hz), 3.95 (d, 2H, J=6.59 Hz), 3.96 (s, 2H), 5.55 (t, 1H, J=6.59 Hz), 6.05 (brs, 1H), 6.95 (dd, 1H, J=7.9, 1.32 Hz), 7.22-7.35 (m, 7H).

Provenance & Evidence