Water → (4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-acetic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of {4-[4-(2-azidoacetyl)-phenyl]-cyclohexyl}-acetic acid ethyl ester (154 mg, 0967 mmol) in 1,4-dioxane (5 mL) is added triphenylphosphine (122 mg, 0.967 mmol) and 1-chloro-3-isothiocyanatobenzene (0.051 mL, 0.389 mmol). The reaction mixture is then heated at 90° C. for 30 min. Water (10 mL) is added and EtOAc (20 mL) is used to extract. The organic phase is washed with brine (1×15 mL), dried with MgSO4, and concentrated to give the title compound (109 mg) as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.19 (t, J=7.20 Hz, 3H) 1.12-1.19 (m, 2H) 1.43-1.52 (m, 2H) 1.81 (d, J=10.61 Hz, 4H) 1.73-1.84 (m, 1H) 2.23 (d, J=6.82 Hz, 2H) 4.07 (q, J=7.07 Hz, 2H) 6.99 (ddd, J=7.83, 2.02, 0.76 Hz, 1H) 7.28-7.36 (m, 3H) 7.41 (s, 1H) 7.47-7.53 (m, 3H) 7.85 (t, J=2.02 Hz, 1H) 10.52 (s, 1H); (M+H)+439.2.

Provenance & Evidence