Sodium Hydroxide → HCID 11592565, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[4′-fluoro-5′-isopropenyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one (Example 300, 50 mg, 0.078 mmol) in DMF (450 μL) was added lithium chloride (13.4 mg, 0.315 mmol). The vial was sealed and the reaction was heated at 160° C. for 14 h. 10% NaOH (10 mL) was added and the resultant solution was extracted with ether (3×10 mL). The aqueous layer was acidified to pH˜3 with 3N HCl and was re-extracted with ether (3×25 mL). The combined organic extracts were washed with brine (25 mL), dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by flash silica gel chromatography (0-25% EtOAc/hexanes gradient) to afford (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[4′-fluoro-2′-hydroxy-5′-isopropenyl-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one as a clear glass. LCMS=622.1 (M+1)+. 1H NMR (CDCl3, 500 MHz, mixture of atropisomers): δ 7.90 (s, 1 H), 7.76-7.70 (m, 4 H), 7.48-7.45 (m, 1 H), 7.11-7.07 (m, 1 H), 6.75 (d, J=11.7 Hz, 1 H), 5.71 (d, J=7.8 Hz, 1 H), 5.59-5.56 (m, 1 H), 5.25-5.21 (m, 2 H), 4.81 (d, J=15.4 Hz, 1 H), 4.04 (d, J=15.6 Hz, 1 H), 3.97-3.92 (m, 1 H), 2.13 (s, 3 H), 0.58 (d, J=6.6 Hz, 3 H).

Provenance & Evidence