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

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).

1. stirringthe reaction mixture was stirred for 1 hr at rt
2. concentrationthe reaction mixture was concentrated
3. customto remove the organic solvent
4. extractionThe aqueous solution was extracted with DCM (3 mL)
5. customto remove organic impurities
6. extractionThe cloudy mixture was extracted with DCM (2×2 mL)
7. dry with materialdried over Na2SO4
8. concentrationconcentrated

ORD record

ord-80edd103be2141818a1a2130da3dc77b

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346852B2