Hydrogen Peroxide → (2R,4E)-6-Benzyloxy-2-propylhex-4-enoic acid

A solution of 24.1 g of (S)-4-benzyl-3-[(2R,4E)-6-benzyloxy-2-propylhex-4-enoyl]oxazolidin-2-one (57.2 mmol) obtained in Example (116a) in a mixed solvent of tetrahydrofuran (800 ml) and water (260 ml) was cooled in an ice bath, and then 35.0 ml of a 30% hydrogen peroxide aqueous solution and 4.83 g of lithium hydroxide monohydrate (115 mmol) were added thereto. The mixture was stirred at the same temperature for 30 minutes, and then raised to room temperature and further stirred for 16 hours. After cooling in an ice bath, 250 ml of a 1.5 M sodium thiosulfate aqueous solution was added to the reaction mixture. The mixture was further stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure, diluted with 500 ml of water and washed with ethyl acetate. Then, the aqueous layer was made acidic with 30 g of sodium dihydrogenphosphate, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure to obtain 13.6 g of the crude title compound.

1. stirringfurther stirred for 16 hours
2. temperatureAfter cooling in an ice bath
3. stirringThe mixture was further stirred at room temperature for one hour
4. concentrationThe reaction mixture was concentrated under reduced pressure
5. additiondiluted with 500 ml of water
6. washwashed with ethyl acetate
7. extractionfollowed by extraction with ethyl acetate
8. washThe organic layer was washed with brine
9. dry with materialdried over anhydrous magnesium sulfate
10. filtrationAfter filtration
11. customthe solvent was evaporated under reduced pressure

ORD record

ord-50d7d2251f384f3782c153630c24e19d

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158790B2