Hydrogen Peroxide → HCID 58388234, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of phenylmethyl {(2S)-2-[(3,4-difluorophenyl)methyl]-3-oxo-3-[(4R)-2-oxo-4-(phenylmethyl)-1,3-oxazolidin-3-yl]propyl}carbamate (548 mg, 1.078 mmol) in tetrahydrofuran (16.200 ml) and Water (5.40 ml) at 0° C. was added H2O2 (0.198 ml, 1.940 mmol)[30 wt %] followed by LiOH (2.69 ml, 2.155 mmol)[0.8M solution]. After 1 h, the solution warmed to 25° C. and stirred 2 h. The reaction mixture was quenched with Na2SO3 solution and the pH was carefully adjusted to ˜3 with 2N HCl solution. The aqueous phase was washed several times with DCM and the combined organic fractions were dried over Na2SO4, concentrated and purified by column chromatography (10-60% EtOAc in hexanes) affording (2S)-3-(3,4-difluorophenyl)-2-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]propanoic acid (260 mg, 0.700 mmol, 64.9% yield) as a clear oil: LCMS (ES) m/e 350 (M+H)+, 1H NMR (400 MHz, DMSO-d6) δ ppm 12.36 (br. s., 1 H) 7.20-7.40 (m, 8 H) 7.03 (br. s., 1 H) 5.02 (s, 2 H) 4.52-4.75 (m, 1 H) 3.01-3.26 (m, 2 H) 2.77 (s, 2 H).

Provenance & Evidence