Trifluoroacetic acid → 1-(Naphthalene-1-ylcarbonyl)-L-Proline

Participants

Reaction Steps

To compound 19 (550 mg, 1.7 mmol) was added a solution of TFA in dichloromethane (95:5, v/v) (4.0 mL). The solution was stirred over a period of 4 h at room temperature under an argon atmosphere. The resulting solution was evaporated under reduced pressure and purified by FCC (CH2Cl2/MeOH, 95:5) to give 415 mg (89%) of title compound 20. 1H NMR (acetone-d6) δ: 2.00 and 2.35 (2m, 3.2 H and 0.8 H, 2×CH2 of proline), 3.66 and 3.74 (2m, 1.6H and 0.4H, CH2N of proline), 4.60 and 4.67 (m, 0.2H and 0.8H, NCHCO of proline), 7.57 (broad, m, 2×CH of naphthalene), 7.67 (d, J=8.4 Hz, 1×CH of naphthalene), 7.95 (broad, m, 2×CH of naphthalene), 8.14 (s, 1×CH of naphthalene). LRMS for C16H16NO3 [M+H]+: 270.0 m/z.

Provenance & Evidence