Triethylamine → Tert-butyl 2-(3-(3-cyclohexylthioureido)phenoxy)ethylcarbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of isothiocyanatocyclohexane (27) (0.16 mL, 1.17 mmol), tert-butyl 2-(3-aminophenoxy)ethylcarbamate (3) (0.282 g, 1.12 mmol), DMAP (0.024 g, 0.196 mmol) and Et3N (0.3 mL, 2.15 mmol) in anhydrous THF was stirred under argon at 50° C. for 24 h. The mixture was concentrated under reduced pressure. Purification by flash chromatography (30% to 60% EtOAc—hexanes gradient) gave tert-butyl 2-(3-(3-cyclohexylthioureido)phenoxy)ethylcarbamate (28) as a white solid. Yield (0.1917 g, 44%); 1H NMR (400 MHz, DMSO-d6) δ 9.29 (s, 1H), 7.59 (br.d, J=7.6 Hz, 1H), 7.15 (t, J=8.2 Hz, 1H), 6.97 (br.t, J=5.5 Hz, 1H), 6.85-6.89 (m, 1H), 6.58-6.63 (m, 1H), 4.06 (br.s, 1H), 3.88 (t, J=5.9 Hz, 2H), 3.25 (q, J=5.7 Hz, 2H), 1.82-1.90 (m, 2H), 1.60-1.70 (m, 2H), 1.47-1.57 (m, 1H), 1.36 (s, 9H), 1.07-1.34 (m, 6H).

Provenance & Evidence