(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one → 2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one (500 mg, 0.837 mmol) in DMF (7.5 mL) was added CuCN (150 mg, 1.67 mmol). The reaction was heated to 100° C. and stirred at that temperature for 14 hours. The reaction was then cooled to room temperature, diluted with EtOAc (200 mL), and washed with 100 mL of 2.5 M aqueous ammonia. The organic layer was washed with brine (75 mL) and then filtered through a plug of silica gel. The filtrate was concentrated, and the residue was purified by flash chromatography on silica gel (5 to 50% EtOAc/hexanes) to afford 2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)benzonitrile. Rf=0.29 (25% EtOAc/hexanes). LCMS=497.0 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.91 (s, 1H), 7.88 (s, 1H), 7.86 (d, J=8.2 Hz, 1H), 7.79 (s, 2H), 7.74 (d, J=8.2 Hz, 1H), 5.78 (d, J=7.8 Hz, 1H), 4.93 (d, J=16.1 Hz, 1H), 4.53 (d, J=15.8 Hz, 1H), 4.23 (m, 1H), 0.86 (d, J=6.7 Hz, 3H).

Provenance & Evidence