Hydrogen Peroxide → (2R)-2-(hydroxymethyl)hexanoic Acid

Temperature

0 °C

To a 2000 mL roundbottom flask was added (4S)-3-[(2R)-2-(hydroxymethyl)hexanoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one (4) (82 g, 0.268 mol) in THF/water (4:1, 750 mL). The solution was cooled to 0° C. and H2O2 (130 mL, 1.07 mol) was added dropwise, followed by lithium hydroxide monohydrate (22.58 g, 0.537 mol) in water (130 mL). The reaction mixture was warmed up to rt and stirred overnight. THF was removed under vacuum, and the aqueous solution was washed with ethyl acetate. The aqueous solution was then acidified to pH ˜3.0 and extracted with ethyl acetate. The extracts were dried (Na2SO4), filtered and concentrated to provide the title compound (42 g, 107%). LCMS: (2M+H)+: 313.2.

1. temperatureThe reaction mixture was warmed up to rt
2. customTHF was removed under vacuum
3. washthe aqueous solution was washed with ethyl acetate
4. extractionextracted with ethyl acetate
5. dry with materialThe extracts were dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-2df847f0cfa5439ca0284b429c69f529

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901119B2