HCID 71227390, compound → HCID 86690221, compound

Participants

Reaction Steps

To a round bottom flask was added ethyl 4-((S)-3-((1R,2R)-2-(benzyloxycarbonylamino)cyclohexylamino)pyrrolidin-1-yl)benzoate trifluoroacetate (30 mg, 0.052 mmol), LiOH monohydrate (37 mg, 1.56 mmol) in water (1 ml) and MeOH (1 ml). The reaction was stirred at rt for 16 hrs. The reaction was concentrated and the residue was purified by RP prep-HPLC to afford methyl 4-((S)-3-((1R,2R)-2-(benzyloxycarbonylamino)cyclohexylamino)pyrrolidin-1-yl)benzoate trifluoroacetate (8 mg, 0.014 mmol, 26.8% yield) as a beige solid. Anal. Calcd. for C26H33N3O4 m/z 451.5, found: 452.3 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 7.90 (d, J=8.8 Hz, 2H), 7.45-7.31 (m, 1H), 7.29-7.15 (m, 4H), 6.67 (d, J=8.8 Hz, 2H), 4.93 (s, 2H), 4.63 (d, J=12.2 Hz, 1H), 4.25-4.11 (m, 1H), 3.72-3.39 (m, 4H), 3.23-3.12 (m, 1H), 2.61-2.42 (m, 1H), 2.40-2.19 (m, 2H), 2.09-1.95 (m, 1H), 1.94-1.77 (m, 2H), 1.63-1.23 (m, 4H).

Provenance & Evidence