Acetonitrile → HCID 178471791, compound

Participants

Reaction Steps

To a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(bromomethyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one (50.4 mg, 0.0894 mmol) in MeCN (1 mL) was added ethyl trans-4-[(ethylamino)methyl]cyclohexanecarboxylate (20 mg, 0.0894 mmol) and i—Pr2NEt (240 μL, 0.179 mmol). The reaction was stirred at room temperature for 16 hours and then concentrated. Purification of the residue by PTLC (50% EtOAc/hexanes) afforded ethyl (trans-4-{[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)benzyl](ethyl)amino]methyl}cyclohexyl)acetate. Rf=0.42 (50% EtOAc/hexanes). LCMS=711.3 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.89 (s, 1H), 7.79 (s, 2H), 7.56-7.52 (m, 2H), 7.48 (s, 1H), 5.73 (d, J=7.8 Hz, 1H), 5.00 (d, J=16.0 Hz, 1H), 4.46 (d, J=16.2 Hz, 1H), 4.11 (q, J=6.9 Hz, 2H), 4.04-3.98 (m, 1H), 3.66-3.53 (m, 2H), 2.47 (q, J=7.1 Hz, 2H), 2.19 (d, J=7.1 Hz, 2H), 2.14 (d, J=7.1 Hz, 2H), 1.80-1.64 (m, 5H), 1.38-1.32 (m, 1H), 1.23 (t, J=7.1 Hz, 3H), 0.99 (t, J=7.1 Hz, 3H), 0.97-0.79 (m, 4H), 0.76 (d, J=6.6 Hz, 3H).

Provenance & Evidence