3-Aminoquinoline → tert-butyl N-[(1R)-1-[(quinolin-3-yl)carbamoyl]-2-[4-(trifluoromethyl)phenyl]ethyl]carbamate

Participants

Reaction Steps

To a solution of (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-[4-(trifluoromethyl)phenyl]propanoic acid XII (0.93 g, 2.79 mmol) and 3-aminoquinoline XIII (0.45 g, 3.10 mmol) in ethyl acetate (30 mL) was added DMT-MM (1.0 g, 3.63 mmol). After being stirred at r.t. overnight, the reaction was washed with water, 1 N HCl, aq. sat. NaHCO3, water and dried over Na2SO4. The solvent was removed under reduced pressure to afford tert-butyl N-[(1R)-1-[(quinolin-3-yl)carbamoyl]-2-[4-(trifluoromethyl)phenyl]ethyl]carbamate (1.19 g, 2.59 mmol, 93% yield). 1H NMR (DMSO-d6) 1.31 (s, 9H), 2.95-3.15 (m, 1H), 3.22-3.27 (m, 1H), 4.46-4.52 (m, 1H), 7.36 (d, J=8 Hz, 1H), 7.62-7.68 (m, 4H), 7.67 (t, J=8 Hz, 1H), 7.83 (t, J=8 Hz, 1H), 8.13 (t, J=7 Hz, 2H), 8.99 (d, J=2 Hz, 1H), 9.24 (d, J=2 Hz, 1H), 11.18 (s, 1H); ESIMS found for C24H24N3O3F3 m/z 460 (M+H).

Provenance & Evidence