HCID 66716745, compound → HCID 11562778, compound

Participants

Reaction Steps

The solution of (4S,5R)-5-[3-(1,3-dioxan-2-yl)phenyl]-3-{[4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one (EXAMPLE 210) (380 mg, 0.647 mmol) in THF and 1N HCl (3:1) (4 mL) was stirred at room temperature for 2 h. The reaction mixture was diluted with EtOAc and washed with NaHCO3 and brine. The organic layer was dried and concentrated in vacuo. The crude material was purified by flash chromatography (Si) to provide 3-((4S,5R)-3-{[4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-2-oxo-1,3-oxazolidin-5-yl)benzaldehyde. LCMS calc.=530.19; found=530.4 (M+1)+. 1H NMR (500 MHz, CDCl3, 1:1 mixture of atropisomers) δ 10.03 (s, 1 H); 7.88 (s, 0.5 H); 7.87 (s, 0.5 H); 7.77-7.52 (m, 5 H); 7.37 (d, J=3.5 Hz, 0.5 H); 7.36 (d, J=3.4 Hz, 0.5 H); 7.02 (d, J=8.4 Hz, 0.5 H); 6.99 (d, J=8.4 Hz, 0.5 H); 6.71 (d, J=3.5 Hz, 0.5 H); 6.69 (d, J=3.4 Hz, 0.5 H); 4.17 (d, J=15.8 Hz, 0.5 H); 6.98 (d, J=15.8 Hz, 0.5 H); 3.78 (s, 3 H); 3.85-3.71 (m, 1 H); 3.26-3.19 (m, 1 H); 1.30-1.26 (m, 4.5 H); 1.19 (d, J=6.9 Hz, 1.5 H); 0.53 (d, J=6.6 Hz, 1.5 H); 0.40 (d, J=6.6 Hz, 1.5 H).

Provenance & Evidence