Hydrochloric Acid → 2-{4'-[(4-benzyloxy-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonyl}-L-valine

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Reaction Steps

2-{4′-[(4-Benzyloxy-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonyl}-L-valine methyl ester (0.24 mmol) was dissolved in THF and MeOH (2:1) (0.6 mL). A 5 M solution of LiOH in water (5.0 equiv.) was then added. The reaction was stirred at room temperature overnight. The reaction was diluted with ethyl acetate and acidified with 1N hydrochloric acid. The organic layer was washed with brine (2×), dried (magnesium sulfate), filtered and concentrated to afford 55 mg of the pure 2-{4′-[(4-benzyloxy-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonyl}-L-valine. LCMS MH+ (m/z) 599. 1H NMR (300 MHz, DMSO-d6): δ 10.55 ppm (s, 1H), 8.08 ppm (d, 1H, J=9.2 Hz), 7.97-7.76 ppm (m, 8 H), 7.58-7.28 ppm (m, 7H), 7.02 ppm (d, 1H, J=8.0 Hz), 5.31 ppm (s, 2H), 3.94 ppm (s, 2H), 3.58-3.52 ppm (m, 1H), 1.96-1.90 ppm (m, 1H), 0.84 ppm (d, 3H, J=7.0 Hz), 0.81 ppm (d, 3H, J=7.0 Hz).

Provenance & Evidence