Trifluoroacetic acid → HCID 67075982, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 2-(5-(tert-butoxycarbonyloxy)-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl(2-(N-cyclohexyl-3-(3-(1-methyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanamido)ethyl)carbamate [Example 5, Step iv)] (290 mg), DCM (5 mL) and TFA (2.5 mL) was stirred at 25° C. for 30 min. The reaction mixture was evaporated to afford crude product. The crude product was purified by preparative HPLC on a Phenomenex Gemini column using a 15-60% gradient of aqueous 0.1% trifluoroacetic acid in acetonitrile as eluent to afford the titled compound as a white solid (94 mg). MS [M+H]+=591.3 (calc=591.3295) (MultiMode+) 1H NMR (400 MHz, CD3OD) δ 8.21 (s, 1H), 7.69 (s, 1H), 7.57 (dt, J=1.6 and 8.0 Hz, 1H), 7.32 (t, J=7.6 Hz, 1H), 7.19 (d, J=7.6 Hz, 1H), 6.69 (d, J=8.2 Hz, 1H), 6.47 (d, J=8.5 Hz, 1H), 4.60 (s, 2H), 4.12 (s, 3H), 3.75-3.64 (m, 5H), 3.52-3.44 (m, 2H), 3.12 (t, J=7.3 Hz, 2H), 3.02 (t, J=5.6 Hz, 2H), 2.88 (t, J=6.7 Hz, 2H), 2.86 (t, J=7.0 Hz, 2H), 2.63 (t, J=5.9 Hz, 2H), 1.80-1.72 (m, 2H), 1.69-1.58 (m, 2H), 1.46-1.24 (m, 5H), 1.15-1.03 (m, 1H).

Provenance & Evidence