Lithium Hydroxide → (S)-3-methyl-2-{4'-[(3-methyl-4-pyridin-3-yl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid

Participants

Reaction Steps

To 100 mg of (S)-3-methyl-2-{4′-[(3-methyl-4-pyridin-3-yl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid methyl ester was dissolved in 1 mL of THF was added 3 mL of LiOH solution (3.6 g LiOH/50 mL MeOH/50 mL H2O). The mixture was stirred at room temperature for 4 days. The solvents were removed under vacuum and the residue was dissolved in 5 mL of water. The pH of the solution was adjusted to 7 and the resulting suspension was filtered. The solid product was dried under vacuum to give 75 mg of (S)-3-methyl-2-{4′-[(3-methyl-4-pyridin-3-yl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid, obtained as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.8 (dd, J=12.6, 6.8 Hz, 6 H) 2.0 (m, 1 H) 2.2 (s, 3 H) 3.6 (dd, J=9.3 Hz, 1 H) 7.3 (dd, J=7.3, 1.0 Hz, 1 H) 7.5 (m, 1 H) 7.6 (dd, J=8.3, 7.6 Hz, 1 H) 7.8 (m, 3 H) 7.9 (m, 4 H) 7.9 (m, 1 H) 8.0 (d, J=8.8 Hz, 2 H) 8.1 (d, J=9.1 Hz, 1 H) 8.7 (m, 2 H) 10.6 (s, 1 H) 12.6 (s, 1 H).

Provenance & Evidence