Water → HCID 178446404, compound

Participants

Reaction Steps

tert-Butyl isocyanide (404 mg, 0.55 mL, 4.86 mmol) was added to a stirred slurry of cis-1-{4-[2-(4-chlorophenyl)-[1,3]-dioxolan-2-yl]-cyclohexyl}pent-4-en-1-one (1.13 g, 3.24 mmol) and ammonium acetate (999 mg, 12.96 mmol) in 2,2,2-trifluoroethanol (0.5 mL), and the resultant slurry was stirred at room temperature. After 8 days the reaction was poured into water and extracted with ethyl acetate (3×). The combined organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Purification by flash column chromatography (silica gel, 10-50% ethyl acetate in heptane) gave cis-2-acetylamino-2-{4-[2-(4-chlorophenyl)-[1,3]-dioxolan-2-yl]-cyclohexyl}hex-5-enoic acid, tert-butylamide as a colorless oil (1.16 g, 71%); 1H NMR (CDCl3, 300 MHz) δ 7.29 (m, 4H), 6.96 (br s, 1H NH), 5.76 (m, 1H), 5.44 (br s, NH, 1H), 4.94 (m, 2H), 3.94 (m, 2H), 3.68 (m, 2H), 2.93 (ddd, J1=16.5 hz, J2=11.5 Hz, J3=5.0 Hz, 1H), 1.90-2.08 (m, 2H), 1.96 (s, 3H), 1.60-1.86 (m, (6H), 1.42 (m, 1H), 1.34 (s, 9H), 1.06 (m, 3H) and 0.86 (m, 1H).

Provenance & Evidence