HCID 59316974, compound → HCID 59316982, compound

Participants

Reaction Steps

A solution of tert-butyl 3-(3-(3,3-dipropylureido)phenyl)prop-2-ynylcarbamate (25) (0.17 g, 0.455 mmol) in EtOH (10 mL) was degassed with vacuum/Ar. Pd/C (10%, 0.0293 g) was added and the atmosphere was purged with H2. The mixture was stirred under H2-filled balloon at room temperature for 5 hrs. The reaction mixture was filtered through Celite and concentrated under reduced pressure. The residue was crystallized from EtOAc/hexanes to give tert-butyl 3-(3-(3,3-dipropylureido)phenyl)propylcarbamate (26) as a pale yellow solid. Yield (0.0946 g, 55%); 1H NMR (400 MHz, DMSO-d6) δ 8.00 (s, 1H), 7.22-7.26 (m, 2H), 7.07 (t, J=7.6 Hz, 1H), 6.82 (br.t, J=5.1 Hz, 1H), 6.70-6.74 (m, 1H), 3.21 (t, J=7.4 Hz, 4H), 2.90 (q, J=6.1 Hz, 2H), 2.45 (t, J=8.0 Hz, 2H), 1.61 (m, 2H), 1.48 (sextet, J=7.4 Hz, 4H), 1.35 (s, 9H), 0.82 (t, J=7.4 Hz, 6H).

Provenance & Evidence