Trifluoroacetic acid → HCID 178426693, compound

Participants

Reaction Steps

To 0.8 mmol of {1-(4-carbamoyl-2,6-dimethyl-benzyl)-2-oxo-2-[3-(4-phenyl-1H-imidazol-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethyl}-carbamic acid tert-butyl ester cooled in an ice bath under argon, was added 3 mL of trifluoroacetic acid. After stirring for 3 hours, the reaction mixture was concentrated and purified on a Gilson prep LC system. Obtained 79 mg (0.13 mmol) of the pure S,S isomer of 4-{2-amino-3-oxo-3-[3-(4-phenyl-1H-imidazol-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-propyl}-3,5-dimethyl-benzamide and 58 mg (0.09 mmol) of a mix of diastereomers for a total of 137 mg (0.22 mmol, 28% yield). Data for “pure” isomer (may contain a trace of other isomer as evident by tlc): 1H NMR (300 MHz, CD3OD): δ 1.85 (0.5H, dd), 2.13–2.51 (6H, m), 2.91 (0.4H, dd), 3.18–3.52 (4H, m), 3.70 (0.5H, d), 4.28–4.47 (1H, m), 4.60–5.06 (2.5H, m), 5.62 (0.5H, t), 6.95–7.90 (13H, m).

Provenance & Evidence