Trifluoroacetic acid → HCID 67076170, 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-ethyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanamido)ethyl)carbamate [Example 4, Step vi)] (245 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 (62.3 mg). MS [M+H]+=605.3 (calc=605.3451) (MultiMode+) 1H NMR (400 MHz, CD3OD) δ 8.28 (s, 1H), 7.70 (s, 1H), 7.59 (d, J=7.7 Hz, 1H), 7.32 (t, J=7.8 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), 4.46 (q, J=7.3 Hz, 2H), 3.76-3.62 (m, 5H), 3.48 (t, J=5.7 Hz, 2H), 3.12 (t, J=7.2 Hz, 2H), 3.02 (t, J=5.5 Hz, 2H), 2.92-2.83 (m, 4H), 2.62 (t, J=6.0 Hz, 2H), 1.80-1.56 (m, 4H), 1.55 (t, J=7.3 Hz, 3H), 1.44-1.24 (m, 5H), 1.17-1.02 (m, 1H).

Provenance & Evidence