Hydrochloric Acid → HCID 68589874, compound

Participants

Reaction Steps

A mixture of (4S,5S)-5-{1-[(benzyloxy)methyl]-1H-imidazol-2-yl}-3-{[4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one (EXAMPLE 244) (16.9 mg, 0.028 mmol), 20% palladium hydroxide on carbon (8.3 mg) and 1N HCl (28 uL) in MeOH (1 mL) was stirred under hydrogen (balloon) overnight, after which time it was filtered through Celite and concentrated in vacuo. The crude material was purified by flash chromatography to afford (4S,5R)-3-{[4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-5-(1H-imidazol-2-yl)-4-methyl-1,3-oxazolidin-2-one. LCMS calc.=492.18; found=492.2 (M+1)+. 1H NMR (500 MHz, CDCl3, 1:1 mixture of atropisomers) δ 7.71 (s, 0.5 H); 7.67 (s, 0.5 H); 7.65 (s, 0.5 H); 7.64 (s, 0.5 H); 7.37 (d, J=3.2 Hz, 0.5 H); 7.35 (d, J=3.3 Hz, 0.5 H); 7.09 (d, 2 H); 7.02 (d, J=8.4 Hz, 0.5 H); 6.99 (d, J=8.5 Hz, 0.5 H); 6.72 (d, J=4.3 Hz, 0.5 H); 6.69 (d, J=4.2 Hz, 0.5H); 5.76 (d, J=8.3 Hz, 0.5 H); 5.64 (d, J=8.7 Hz, 0.5 H); 4.72 (d, J=15.8 Hz, 0.5 H); 4.68 (d, J=15.8 Hz, 0.5 H); 4.20 (d, J=15.7 Hz, 0.5 H); 4.01 (d, J=15.7 Hz, 0.5 H); 3.90 (br, s, 1H); 3.79-3.72 (m, 4H); 3.25-3.18 (m, 1 H); 1.28-1.22 (m, 6 H); 0.67 (d, J=6.5 Hz, 1.5 H); 0.59 (d, J=6.5 Hz, 1.5 H).

Provenance & Evidence