Citric Acid → HCID 178464360, compound

Participants

Reaction Steps

To a stirred solution of ethyl (trans-4-{[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)phenyl](ethyl)amino]methyl}cyclohexyl)acetate (Step C; 29 mg; 0.042 mmol) in EtOH (2 mL) was added 4 M KOH (400 μL). The reaction was stirred for 90 min, neutralized with aq. citric acid and partitioned between EtOAc (10 mL) and H2O (10 mL). The aqueous layer was re-extracted with EtOAc (10 mL) and the combined organic layers were washed with brine (10 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by preparatory silica gel chromatography (eluted with 2:1 Hexanes:EtOAc+1% AcOH) to afford (trans-4-{[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)phenyl](ethyl)amino]methyl}cyclohexyl)acetic acid as a clear glass. LCMS=669.2 (M+1)+. 1H NMR (CDCl3, 500 MHz): δ 7.91 (s, 1 H), 7.80 (s, 2 H), 7.57 (s, 1 H), 7.52 (d, J=8.3 Hz, 1H), 7.22 (d, J=8.5 Hz, 1 H), 5.77 (d, J=8.0 Hz, 1 H), 4.79 (d, J=16.2 Hz, 1 H), 4.57 (d, J=16.2 Hz, 1H), 4.02-3.99 (m, 1 H), 3.05-2.95 (m, 2 H), 2.93-2.84 (m, 2 H), 2-19 (d, J=6.9 Hz, 2 H), 1.82-1.75 (m, 4H), 1.74-1.68 (m, 1 H), 1.43-1.37 (m, 1 H), 1.01 (t, J=7.0 Hz, 3 H), 0.99-0.88 (m, 4 H), 0.66 (d, J=6.4 Hz, 3 H).

Provenance & Evidence