Hydrogen Peroxide → HCID 58003529, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-benzyl-3-[2-(4,4″-bis-trifluoromethyl-[1,1′;3′,1″]terphenyl-5′-yl)-4-methyl-pentanoyl]-oxazolidin-2-one (3.66 g, 5.7 mmol) in THF (24 mL) was added water (8 mL). The system was cooled to 0° C. To this cold solution was added LiOH.H2O (240 mg, 5.7 mmol) and 30% H2O2 (1.95 mL, 17.2 mmol), and stirred at 0° C. for 15 min. The excess H2O2 was quenched by adding 1.5 M aqueous Na2SO3 solution (11.5 mL, 17.2 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-(4,4″-bis-trifluoromethyl-[1,1′;3′,1″]terphenyl-5′-yl)-4-methyl-pentanoic acid (2.5 g, 92%).

Provenance & Evidence