Hydrogen Peroxide → (2R,5S)-2-benzyl-5-methylhexanedioic acid

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Reaction Steps

An aqueous solution of 50% H2O2 (0.12 mL, 2.1 mmol) was added to a solution of (2R,5S)-2-benzyl-1,6-bis((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-methylhexane-1,6-dione (200 mg, 0.352 mmol) in THF (3 mL) and water (1 mL) at 0° C. After 5 min of stirring, LiOH.H2O (44 mg, 1.1 mmol) was added and the reaction mixture was stirred for 1 hr at rt. Saturated aqueous Na2SO3 (0.2 mL) and saturated aqueous NaHCO3 (0.2 mL) were added and the reaction mixture was concentrated to remove the organic solvent. The aqueous solution was extracted with DCM (3 mL) to remove organic impurities. The aqueous phase was then acidified using aqueous 5 N HCl to pH<2. The cloudy mixture was extracted with DCM (2×2 mL). The organic extracts were combined, dried over Na2SO4 and concentrated to give (2R,5S)-2-benzyl-5-methylhexanedioic acid (52 mg, 0.21 mmol, 59% yield) as a white powder. Anal. Calcd. for C14H18O4 m/z 250.1. found: 249.2 (M−): 1H NMR (400 MHz, CDCl3) δ ppm 7.28 (m, 2H), 7.17 (m, 3H), 2.99 (m, 1H), 2.75 (m, 1H), 2.65 (m, 1H), 2.4 (m, 1H), 1.79 (m, 1H), 1.63 (m, 2H), 1.44 (m, 1H), 1.15 (d, J=7 Hz, 3H).

Provenance & Evidence