Methanol → 6-[3-methyl-2-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]anilino]-6-oxohexanoic acid

Participants

Reaction Conditions

Reaction Steps

5-{3′-[5-(tert-Butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-biphenyl-2-ylcarbamoyl}-pentanoic acid methyl ester (125 mg, 0.19 mmol, Example 137: step a) and LiOH (12.5 mg, 0.54 mmol) were dissolved into MeOH (3 mL) and heated to 60° C. for 12 hours. The reaction was dissolved into EtOAc and washed with 20% citric acid. The aqueous layers were acidified with acetic acid (pH 3) and extracted with EtOAc. The organic layers were combined and dried (MgSO4) followed by removal of solvents in vacuo. The resulting material was purified by preparative RP-HPLC (0–100% water/acetonitrile—both solvents were free of TFA, 45 minutes, λ=245 nm). 1H-NMR (CDCl3): δ 7.95–7.93 (d, 1H, J=9.3 Hz), 7.81–7.78 (d, 1H, J=7.91 Hz), 7.63–7.59 (m, 1H), 7.55–7.53 (t, 1H, J=8.35, Hz, J=7.59 Hz), 7.38–7.36 (d, 1H, J=9.35 Hz), 7.25–7.21 (m, 1H), 7.07–7.05 (d, 1H, J=7.07 Hz), 6.78 (s, 1H), 3.55 (s, 2H), 2.51 (s, 3H), 2.15–2.12 (m, 2H), 1.96–1.95 (m, 2H), 1.93 (s, 3H).

Provenance & Evidence