Hydrochloric Acid → 3-Phenyl-3-{5-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-indol-1-yl}-propionic acid

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Reaction Conditions

Reaction Steps

A mixture of 3-phenyl-3-{5-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-indol-1-yl}-propionic acid ethyl ester (0.020 g, 0.04 mmol) and sodium hydroxide (0.01 g, 0.25 mmol) in THF/H2O [1/0.3] (1.3 mL) was stirred at 50° C. for 24 h. The reaction mixture was neutralized with 1.0 N HCl to pH 5 and extracted with ethyl acetate. After removal of solvent, the crude product was purified via column chromatography, eluting with methylene chloride/methanol (95/5) to give the title compound (15% yield) as white solid. 1H NMR (CDCl3) δ 10.76 (br, 1H), 8.16 (br, 1H), 7.57 (br, 1H), 7.10-7.45 (m, 8H), 7.03 (m, 1H), 6.95 (m, 2H), 6.18 (m, 1H), 3.38 (m, 2H), 3.21 (m, 2H), 2.61 (m, 2H), 2.43 (m, 2H), 2.03 (m, 2H), 1.82 (m 2H), 1.70 (m, 2H). Mass Spectrum (LCMS, ESI) calculated for C28H30N3O2 440.2 (M+H); found 440.3.

Provenance & Evidence