Sodium Thiosulfate → HCID 69720245, compound

Participants

Reaction Steps

36 mg of methyl (3S,4S)-4-[N-{(1R,2R,4E)-5-(2-benzoxazolyl)-1-methyl-2-(3,4-methylenedioxyphenyl)-4-pentenyl}-N-(2-naphthylmethyl)carbamoyl]-3-tert-butoxycarbonyl-4-hydroxybutanoate in 2 ml of chloroform was stirred with 42 mg of the Dess-Martin reagent (periodenane) at room temperature for 1 hour. The reaction solution was poured into a mixture of saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium thiosulfate and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was evaporated in vacuo. The residue was purified by silica gel thin layer chromatography [Kieselgel™ 60F254, Art™ 5744; hexane/ethyl acetate=3/2] to give 14.7 mg (yield 41%) of the title compound as a colorless oily substance.

Provenance & Evidence