Lithium Hydroxide → (S)-2-{4'-[(5-Acetyl-4-hydroxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid

Participants

Reaction Steps

To (S)-2-{4′-[(5-acetyl-4-hydroxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester (15 mg) was added 0.5 mL of THF and 2 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 2 mL of water was added. The aqueous solution was acidified and the resulting solid was collected through filtration to give 7 mg of (S)-2-{4′-[(5-acetyl-4-hydroxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.8 (dd, J=12.4, 6.8 Hz, 6 H) 1.9 (m, 1 H) 2.7 (s, 3 H) 2.8 (s, 3 H) 3.6 (dd, J=9.3, 6.1 Hz, 1 H) 7.3 (d, J=9.1 Hz, 1 H) 7.8 (d, J=8.8 Hz, 2 H) 7.9 (m, 4 H) 8.0 (d, J=8.8 Hz, 2 H) 8.1 (dd, J=9.1, 3.8 Hz, 2 H) 10.5 (s, 1 H) 13.7 (s, 1 H).

Provenance & Evidence