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

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Reaction Steps

A solution of 18.7 g of (S)-4-benzyl-3-[(2R,4E)-6-benzyloxy-2-methylhex-4-enoyl]oxazolidin-2-one (47.5 mmol) obtained in Example (76a) in a mixed solvent of tetrahydrofuran (700 ml) and water (230 ml) was cooled in an ice bath, and then 30.0 ml of a 30% hydrogen peroxide aqueous solution and 4.15 g of lithium hydroxide monohydrate (95.3 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 11.0 g of the crude title compound.

Provenance & Evidence