Trifluoroacetic acid → Trifluoroacetic acid

Participants

Reaction Steps

A stirring solution of tert-butyl (1R,3R,4S)-3-acetamido-4-((S)-2-oxo-3-(6-(trifluoromethyl)quinazolin-4-ylamino)pyrrolidin-1-yl)cyclohexylcarbamate (1.65 g, 3 mmol) in dichloromethane (8 mL) was charged with trifluoroacetic acid (4 mL). The reaction was stirred for 1 h at room temperature and concentrated in vacuo. The residue was dissolved in a mixture of 1 mL of methanol and 5 mL of dichloromethane. The resulting solution was added dropwise to 80 mL of t-butylmethylether with stirring. The solid formed was collected with filtration and dried to give the title compound as its TFA salt (1.75 g, 86%). LC/MS found [M+H]+=451. 1H-NMR (400 MHz, CD3OD), δ ppm: 8.82 (1H, s), 8.77 (1H, s), 8.20-8.27 (1H, m), 7.95 (1H, d, J=8.65 Hz), 5.32 (1H, t, J=9.92 Hz), 4.36 (1H, t, J=4.07 Hz), 4.16-4.23 (1H, m), 3.87 (1H, t, J=9.16 Hz), 3.70-3.79 (1H, m), 3.39 (1H, s), 2.54-2.67 (1H, m), 2.32-2.45 (1H, m), 2.08-2.23 (2H, m), 1.88-2.04 (6H, m), 1.73-1.87 (1H, m).

Provenance & Evidence