Sodium Hydroxide → HCID 178444618, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-ethyl 3-(4-fluorophenyl)-2-hydroxy-2-(5-(methylsulfonamido)-1H-benzo[d]imidazol-2-yl)propanoate (50 mg, 0.12 mmol) in THF (0.5 ml) at rt were added (R)-2-isocyanatoheptane (25 mg, 0.18 mmol) and NaOH (6 mg, 0.15 mmol). The mixture was heated at 70° C. for 25 min. The resulting mixture was filtered through a short plug of silica and concentrated. The resulting residue was purified by Combiflash (silica gel column, 5-35% ethyl acetate in hexane) to give the title product. LC/MS (m/z): 517.0 [M+1]; 1H NMR (400 MHz, CDCl3) δ 10.8-10.9 (d, 1H), 7.6 (t, 1H), 7.5 (s, 1H), 7.3 (m, 1H), 7.2 (m, 2H), 6.9 (m, 2H), 3.7-3.8 (m, 2H), 3.5 (d, 1H), 2.9 (s, 3H), 1.3 (q, 2H), 0.9-1.1 (m, 5H), 0.6-0.9 (m, 7H);

Provenance & Evidence