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

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Reaction Steps

To 41 mg of (S)-3-methyl-2-(4′-{[3-methyl-4-(3-nitro-phenyl)-benzofuran-2-carbonyl]-amino}-biphenyl-4-sulfonylamino)-butyric acid methyl ester dissolved in 0.5 mL of THF was added 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 the residue was dissolved in 5 mL of water. The solution was acidified and the resulting suspension was filtered. The solid product was dried under vacuum to give 29 mg of (S)-3-methyl-2-(4′-{[3-methyl-4-(3-nitro-phenyl)-benzofuran-2-carbonyl]-amino}-biphenyl-4-sulfonylamino)-butyric acid, obtained as pale brown 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) 2.2 (s, 3 H) 3.6 (dd, J=9.3, 6.1 Hz, 1 H) 7.3 (dd, J=7.3, 0.8 Hz, 1 H) 7.6 (dd, J=8.3, 7.3 Hz, 1 H) 7.8 (m, 8 H) 8.0 (d, J=8.8 Hz, 3 H) 8.1 (d, J=9.3 Hz, 1 H) 8.3 (t, J=1.9 Hz, 1 H) 8.3 (m, 1 H) 10.6 (s, 1 H) 12.6 (s, 1 H).

Provenance & Evidence