Sodium hydride → (6S)-3-{[2'-chloro-5'-isopropyl-4-(trifluoromethyl)biphenyl-2-yl]methyl}-6-(2-methylphenyl)-1,3-oxazinan-2-one

Participants

Reaction Steps

(6S)-6-(2-methylphenyl)-1,3-oxazinan-2-one (prepared from ethyl-4-(2-methylphenyl)-4-oxobutyrate by a procedure analogous to that reported for Intermediate 21; 20 mg; 0.10 mmol) was treated with sodium hydride (60% in oil; 8.0 mg; 0.20 mmol) and 2-(bromomethyl)-2′-chloro-5′-isopropyl-4-(trifluoromethyl)biphenyl (Intermediate 27; 41 mg; 0.10 mmol) as described in Example 11 to afford (6S)-3-{[2′-chloro-5′-isopropyl-4-(trifluoromethyl)biphenyl-2-yl]methyl}-6-(2-methylphenyl)-1,3-oxazinan-2-one as a white solid. LCMS=502.1 (M+1)+. 1H NMR (CDCl3, 500 MHz, mixture of atropisomers): δ 7.78 (s, 1H), 7.67-7.64 (m, 1H), 7.48 (d, J=8.1 Hz, 1H), 7.45 (s, 1H), 7.40-7.37 (m, 1H), 7.28-7.24 (m, 3H), 7.19-7.17 (m, 1H), 7.11 (dd, J=8, 2.1 Hz, 1H), 5.51 (dd, J=9.9, 2.8 Hz, 1H), 4.69 (d, J=15.8 Hz, 1H), 4.45 (d, J=15.8 Hz, 1H), 3.31-3.21 (m, 1H), 3.14-3.10 (m, 1H), 2.98-2.93 (m, 1H), 2.35 (s, 3H), 2.20-2.15 (m, 1H), 2.14-2.04 (m, 1H) 1.29 (d, J=6.9 Hz, 6H).

Provenance & Evidence