Potassium Hydroxide → HCID 178461487, compound

Participants

Reaction Steps

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-(trifluoromethoxy)phenyl](methyl)amino]carbonyl}cyclohexyl)acetate (100 mg; 0.14 mmol) in EtOH (110 mL) was treated dropwise with 4 M KOH (1 mL). The reaction was stirred at room temperature and quenched with 10% citric acid after 2.5 h. The reaction was partitioned between EtOAc (50 mL) and H2O (50 mL) and the aqueous layer was extracted with EtOAc (3×50 mL). The combined extracts were washed with brine (50 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by reverse-phase HPLC and the desired product was lyophilized to afford (trans-4-{[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl](methyl)amino]carbonyl}cyclohexyl)acetic acid as a white solid. LCMS=685.0 (M+1)+. 1H NMR (CDCl3, 500 MHz, mixture of atropisomers): δ 7.92 (s, 1 H), 7.80 (s, 1 H), 7.74 (s, 1 H), 7.29-7.21 (m, 2 H), 7.17-7.15 (m, 1 H), 5.67 (d, J=8.2 Hz, 1 H), 4.96 (d, J=14.7 Hz, 1 H), 4.22 (d, J=16.5 Hz, 1 H), 3.88 (d, J=15.1 Hz, 1 H), 3.41 (s, 3 H), 2.73-2.66 (m, 1 H), 2.28-2.24 (m, 1 H), 2.15-2.12 (m, 1 H), 2.01-1.50 (m, 8 H), 1.18-1.10 (m, 1 H), 0.76-0.68 (m, 3 H).

Provenance & Evidence