(4S,5R)-3-({3-[3'-acetyl-4'-(benzyloxy)-4-methoxybiphenyl-3-yl]-6-azetidin-1-ylpyridin-2-yl}methyl)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one → (4S,5R)-3-{[3-(3'-acetyl-4'-hydroxy-4-methoxybiphenyl-3-yl)-6-azetidin-1-ylpyridin-2-yl]methyl}-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one

Participants

Reaction Steps

A mixture of (4S,5R)-3-({3-[3′-acetyl-4′-(benzyloxy)-4-methoxybiphenyl-3-yl]-6-azetidin-1-ylpyridin-2-yl}methyl)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (EXAMPLE 257 Step A) (42 mg, 0.053 mmol) and 10% Pd/C (20 mg, 0.053 mmol) in EtOAc (2 ml) was degassed and flushed with H2 using a balloon. The mixture was stirred at RT under H2 for 6 hours, then, flushed with nitrogen, and filtered washing with EtOAc. The filtrate was concentrated and the residue purified by TLC eluting with 3:2 hexanes/EtOAc to afford the title compound. Mass spectrum (ESI) 700.2 (M+1). 1H NMR (500 MHz, CD3OD): (atropisomers) δ 8.05 (s, 1H); 7.96 (s, 1H); 7.91-7.70 (m, 3H); 7.61 (dd, J=2.3, 8.7 Hz, 1H); 7.49-7.36 (m, 2H); 7.13 (d, J=8.2 Hz, 1H); 6.98 (d, J=8.7 Hz, 1H); 6.38 (d, J=8.5 Hz, 1H); 5.70 (br d, J=75.7 Hz, 1H); 4.69 (m, 1H); 4.43-3.73 (m, 9H); 2.68 (s, 3H); 2.42 (m, 2H); 0.65 (br d, J=37.5 Hz, 3H).

Provenance & Evidence