p-Toluenesulfonic acid → 5-[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl](ethyl)amino]pentanal

To a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-[[4-(5,5-dimethyl-1,3-dioxan-2-yl)butyl](ethyl)amino]-5-(trifluoromethoxy)benzyl]-4-methyl-1,3-oxazolidin-2-one (20 mg, 0.0286 mmol) in THF (3 mL) and water (1 mL) was added p-toluene sulfonic acid (excess). The reaction was stirred at room temperature for 16 hours, and then brought to reflux and stirred for 24 hours. The mixture was diluted with EtOAc (20 mL) and washed with saturated NaHCO3 solution and brine (10 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by PTLC (35% EtOAc/hexanes) afforded 5-[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl](ethyl)amino]pentanal. Rf=0.24 (35% EtOAc/hexanes). LCMS=615.2 (M+1)+. 1H NMR (CDCl3, 500 MHz), 9.72 (s, 1H), 7.89 (s, 1H), 7.79 (s, 2H), 7.19-7.12 (m, 3H), 5.73 (d, J=8.2 Hz, 1H), 4.73 (d, J=16.3 Hz, 1H), 4.53 (d, J=16.0 Hz, 1H), 4.04-4.00 (m, 1H), 2.95-2.85 (m, 4H), 2.42 (t, J=7.1 Hz, 2H), 1.61-1.37 (m, 4H), 0.98 (t, J=7.1 Hz, 3H), 0.67 (d, J=6.6 Hz, 3H).

1. temperatureto reflux
2. stirringstirred for 24 hours
3. washwashed with saturated NaHCO3 solution and brine (10 mL each)
4. dry with materialThe organic layer was dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customPurification of the residue by PTLC (35% EtOAc/hexanes)

ORD 기록

ord-8d2c802a1b8045179dda7aff71bb4ec7

출처 데이터셋

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07781426B2