Hydrogen Peroxide → (S)-3-((Tert-butoxycarbonyl)amino)-2-(4-chlorobenzyl)propanoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of [(2S)-2-(4-Chlorobenzyl)-3-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-3-oxo-propyl]-carbamic acid tert-butyl ester (300 mg, 0.63 mmol) in THF/H2O (30/10 mL) at 0° C. was added LiOH (80 mg, 1.9 mmol) and H2O2 (30% by volume, 3.0 mL, 0.63 mmol) and stirred at 0° C. for 30 minutes. Then Na2SO3 (saturated solution, 10 mL) was added slowly & cautiously. Diluted with EtOAc (100 mL) and extracted into water (2×100 mL) The aq. layer was acidified (1N HCl) and extracted into EtOAc (3×100 mL) Dried over Na2SO4 and concentrated in vacuo to give (S)-2-(tert-Butoxycarbonylamino-methyl)-3-(4-chlorophenyl)-propionic acid (150 mg, 75%.) LCMS (APCI−) m/z 322 [M-Boc+H]−; Rt: 2.23 min

Provenance & Evidence