Hydrogen Peroxide → HCID 57754958, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-benzyl-3-{2-[5-(2,5-bis-trifluoromethyl-phenylamino)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoyl}-oxazolidin-2-one (2.55 g, 3.53 mmol) in THF (15 mL) was added water (5 mL). The system was cooled to 0° C. To this cold solution was added LiOH.H2O (148 mg, 3.53 mmol) and 30% H2O2 (1.20 mL, 10.59 mmol,) and stirred at 0° C. for 15 min. The excess H2O2 was quenched by adding 1.5 M aqueous Na2SO3 solution (7.06 mL, 10.59 mmol) and stirred at room temperature for 10 min. The organic solvent was removed in vacuo. The resulting liquid was acidified to pH=2 by adding 1 N aqueous HCl solution. The aqueous layer was extracted with EtOAc (3×50 mL) and dried (MgSO4). The mixture was concentrated in vacuo to receive a crude mixture which was purified by ISCO silica gel column chromatography to yield (R) 2-[5-(2,5-Bis-trifluoromethyl-phenylamino)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid (1.15 g, 58%).

Provenance & Evidence