Trifluoroacetic acid → 4-[2'-(1-Hydroxy-ethyl)-biphenyl-3-sulfonyl]-5-methylsulfanyl-thiophene-2-carboxamidine trifluoroacetate

Participants

Reaction Steps

{Imino-[5-methylsulfanyl-4-(2′-vinyl-biphenyl-3-sulfonyl)-thiophen-2-yl]-methyl}-carbamic acid tert-butyl ester (25 mg, 0.05 mmol) was treated with trifluoroacetic acid (50% in DCM) for 1 hr at rt. The reaction mixture was concentrated in vacuo and then basified with 1 M NaOH to pH 8 and allowed to stand for 10 min. The solution was then re-acidified with TFA and purified using C18-HPLC (10–80% CH3CN in H2O (0.1% TFA) over 30 min) to give 7 mg (33%) of the title compound as a white solid (Rt: 12.3 min). 1H-NMR (CD3OD): δ 8.32 (s, 1H), 8.01–8.05 (m, 1H), 7.98–8.00 (m, 1H), 7.64–7.71 (m, 3H), 7.44–7.49 (m, 1H), 7.32–7.36 (m, 1H), 7.16–7.18 (m, 1H), 4.75 (q, 1H, J=6.5 Hz), 2.72 (s, 3H), 1.28 (d, 3H, J=6.5 Hz). ESI-MS (m/z): Calcd. for C20H20N2O3S3: 433.6 (M+H); found: 433.1.

Provenance & Evidence