Trifluoroacetic acid → Trifluoroacetic acid

Participants

Reaction Steps

A mixture of 2-((R)-(3-chlorophenyl)((R)-1-((S)-1-cyclohexyl-3-(2-(trimethylsilyl)ethoxycarbonylmethylamino)propan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethyl carbamate (0.0250 g, 0.038 mmol) and trifluoroacetic acid (1 mL) in CH2Cl2 (5 mL) was stirred at rt for 3 h. After the solvents were removed in vacuo, the residue was purified by reversed-phase HPLC (Phenomenex® Luna 5μ C18(2) 100 A, 250×21.20 mm, 5 micron, 10%→90% CH3CN/H2O, 0.1% CF3COOH over 13 min, flow rate 25 mL/min) to give 2-((R)-(3-chlorophenyl)((R)-1-((S)-1-cyclohexyl-3-(methylamino)propan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethyl carbamate as its TFA salt (0.0205 g, 86%). LC-MS (3 min) tR=1.49 min, m/z 511, 509 (MH+); 1H NMR (400 MHz, CD3OD) δ 7.28-7.12 (m, 4H), 4.20 (d, J=13.2 Hz, 1H), 4.11-3.99 (m, 3H), 3.95 (d, J=8.8 Hz, 1H), 3.87 (d, J=13.2 Hz, 1H), 3.40-3.28 (m, 2H), 2.96 (dd, J=12.6, 3.2 Hz, 1H), 2.84 (dd, J=12.6, 10.2 Hz, 1H), 2.73-2.63 (m, 2H), 2.61 (s, 3H), 1.71-0.75 (m, 18H).

Provenance & Evidence