Hydrogen Peroxide → HCID 68768818, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (4R)-4-benzyl-3-[(2R,3R)-3-(4-chloro-phenyl)-3-hydroxy-2-methyl-propionyl]-oxazolidin-2-one (1.32 g, 3.53 mmol) in 4:1 THF/water (20 mL) was cooled to 0° C. and treated with 30% aq. H2O2 (1.5 mL, 13.2 mmol) and LiOH (1 M in water, 5.6 mL, 5.6 mmol). The reaction mixture was stirred for 1 h at 0° C., and then a solution of Na2SO3 (1.76 g, 14 mmol) in water (10 mL) was added. The mixture was concentrated at a temperature<30° C. The aqueous layer was extracted with DCM (3×), then was acidified with conc. HCl and extracted with EtOAc (4×). The combined EtOAc layers were dried (Na2SO4) and concentrated to give the crude acid, which was used without further purification (0.76 g, quant.). 1H NMR (500 MHz, CDCl3): 7.36-7.32 (m, 2H), 7.32-7.28 (m, 2H), 5.16 (d, J=3.9, 1H), 2.81 (dq, J=7.2, 3.9, 1H), 1.15 (d, J=7.2, 3H).

Provenance & Evidence