Sodium hydride → (4S)-3-{[4'-fluoro-5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-(4-methylbenzyl)-1,3-oxazolidin-2-one

Participants

Reaction Steps

(4S)-4-(4-methylbenzyl)-1,3-oxazolidin-2-one (Step B, 14 mg, 0.074 mmol) was treated with sodium hydride (60% in oil, 6.2 mg, 0.154 mmol) and 2′-(bromomethyl)-4-fluoro-5-isopropyl-2-methoxy-4′-(trifluoromethyl)biphenyl (Intermediate 10, 25 mg, 0.062 mmol) as described in Example 305 to afford (4S)-3-{[4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-(4-methylbenzyl)-1,3-oxazolidin-2-one as clear gum. LCMS=516.4 (M+1)+. 1H NMR (CDCl3, 500 MHz, mixture of atropisomers) δ 7.65-7.60 (m, 1H), 7.53 (s, 1H), 7.35-7.32 (m, 1H), 7.06-7.20 (m, 2H), 6.82-6.75 (m, 2H), 6.69 (d, J=11.7 Hz, 1H), 4.67 (d, J=15.8 Hz, 1H), 4.06 (d, J=15.8 Hz, 1H), 4.04-4.00 (m, 1H), 3.96-3.93 (m, 1H), 3.73 (s, 3H), 3.55-3.48 (m, 1H), 3.23-3.15 (m, 1H), 2.63 (dd, J=13.5, 3.6 Hz, 1H), 2.35 (d, J=13.5 Hz, 1H), 2.29 (s, 3H), 1.25-1.13 (m, 6H).

Provenance & Evidence