Trifluoroacetic acid → HCID 178513033, compound

Participants

Reaction Steps

Trifluoroacetic acid (2 mL) was added to a stirred solution of (2R)-2-[2,3-bis-(tert-butoxycarbonyl)guanidino]-3-(4′-dibenzofuran-4-yl-biphenyl-4-ylmethylsulfanyl)-propionic acid (250 mg, 0.36 mmol) in anhydrous dichloromethane (10 mL). The reaction was stirred for 4 hours (HPLC control) and then concentrated in vacuo. The resultant brown oil was reconstituted and concentrated from methanol (3×10 mL) and then from dichloromethane (2×10 mL) to give the title compound as an off-white solid (175 mg, 99%): Rf=0.20 (10% methanol in dichloromethane). 1H NMR (DMSO-d6, 300 MHz): δ 8.19 (1H, d, J=8 Hz, Ar—H), 8.13 (1H, d, J=9 Hz, Ar—H), 8.02 (2H, d, J=9 Hz, Ar—H), 7.84 (3H, m, Ar—H), 7.74 (4H, m, 2×Ar—H, 2×NH), 7.53 (3H, m, Ar—H), 7.42 (3H, m, Ar—H), 7.26 (1H, d, J=9 Hz, NH), 7.10 (1H, br s, NH), 4.58 (1H, m, CHN), 3.86 (2H, s, PhCH2S), 2.92 (1H, dd, J=15, 5 Hz, CHHCHN), 2.75 (1H, dd, J=15, 7 Hz, CHHCHN); ESI-LCMS e/z calcd for C29H25N3O3S 495.600, found 496 (M+H)+.

Provenance & Evidence