Acetic Acid → 3-{3-[6-azetidin-1-yl-2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)pyridin-3-yl]-4-methoxyphenyl}propanoic acid

Participants

Reaction Steps

Methyl 3-{3-[6-azetidin-1-yl-2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)pyridin-3-yl]-4-methoxyphenyl}propanoate (93 mg, 0.143 mmol) was dissolved in dioxane (2 mL) and water (0.5 mL). As the solution was stirred vigorously, 1M lithium hydroxide (0.285 mL, 0.285 mmol) was added dropwise. The reaction was stirred at room temperature for 1 hr and then quenched with acetic acid (0.020 mL, 0.357 mmol). The reaction was diluted with ethyl acetate (15 mL) and washed with water (2×10 mL) and brine (10 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was redissolved in dichloromethane (2 mL) and heptanes (2 mL) and concentrated again. Purification of the residue by flash chromatography on silica gel (0 to 100% ethyl acetate/hexanes) afforded 3-{3-[6-azetidin-1-yl-2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)pyridin-3-yl]-4-methoxyphenyl}propanoic acid. LCMS=638.2 (M+H)+. 1H NMR (CDCl3, 500 MHz) δ 7.85 (s, 1H), 7.72 (s, 2H), 7.30 (d, J=8.7 Hz, 1H), 7.17 (dd, J=8.4, 2.2 Hz, 1H), 7.00 (bs, 1H), 6.87 (d, J=8.4 Hz, 1H), 6.27 (d, J=8.3 Hz, 1H), 5.61 (bs, 1H), 4.8-4.4 (m, 2H), 4.07 (m, 4H), 3.85 (m, 1H), 3.75 (s, 3H), 2.92 (m, 2H), 2.64 (m, 2H), 2.41 (m, 2H), 0.75-0.58 (m, 3H).

Provenance & Evidence