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

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Reaction Steps

To 100 mg of (S)-2-{4′-[(4-ethoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester 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 solution was acidified and the resulting suspension was filtered. The solid product was dried under vacuum to give 84 mg (86% yield) of (S)-3-methyl-2-{4′-[(3-methyl-4-propoxy-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=12.9, 6.8 Hz, 6 H) 1.1 (t, J=7.3 Hz, 3 H) 1.8 (m, 2 H) 2.0 (m, 1 H) 2.8 (s, 3 H) 3.6 (dd, J=9.1, 6.1 Hz, 1 H) 4.1 (t, J=6.2 Hz, 2 H) 6.8 (d, J=8.1 Hz, 1 H) 7.2 (d, J=8.1 Hz, 1 H) 7.4 (t, J=8.2 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 (d, J=9.3 Hz, 1 H) 10.5 (s, 1 H) 12.6 (s, 1 H).

Provenance & Evidence