Potassium Hydroxide → HCID 178464364, compound

Participants

Reaction Steps

To a 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-(trifluoromethoxy)phenyl](ethyl)amino]methyl}cyclohexyl)acetate (29 mg, 0.0407 mmol) in EtOH (1 mL) was added 4 M KOH (100 μL). The reaction was stirred at room temperature for 30 minutes and 4 M KOH (100 μL) was added. After an additional 30 minutes 4 M KOH (100 μL) was added. After 30 min the reaction was quenched with 1 N HCl (1.5 mL) and then neutralized with saturated NaHCO3 solution. The mixture was extracted with EtOAc (2×20 mL) and washed with brine. The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by PTLC (EtOAc+1% AcOH) afforded (trans-4-{[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl](ethyl)amino]methyl}cyclohexyl)acetic acid. Rf=0.94 (EtOAc+1% AcOH). LCMS=685.3 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.91 (s, 1H), 7.80 (s, 2H), 7.20-7.12 (m, 3H), 5.76 (d, J=8.1 Hz, 1H), 4.74 (d, J=16.3 Hz, 1H), 4.59 (d, J=16.3 Hz, 1H), 4.04-4.00 (m, 1H), 2.97-2.75 (m, 4H), 1.81-0.88 (m, 15H), 0.66 (d, J=6.5 Hz, 3H).

Provenance & Evidence