Triacetoxyperiodinane → Sar-114137

Participants

Reaction Steps

A solution of N-{(S)-1-[Hydroxy-(5-phenyl-1,2,4-oxadiazol-3-yl)-methyl]-propyl}-2-(2-methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyramide (41 mg, 0.076 mmol) in methylene chloride (6 mL) was treated with Dess-Martin periodinane (39 mg, 0.092 mmol) and stirred at room temperature for 90 minutes. The reaction mixture was washed with a solution of Na2S2O3 in water (0.26M), saturated aqueous bicarbonate solution and water, dried over Na2SO4 and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography eluting with a mixture of ethyl acetate and heptane to give 2-(2-Methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-N-[(S)-1-(5-phenyl-1,2,4-oxadiazole-3-carbonyl)-propyl]-butyramide as an off white solid (18 mg) (mixture of diastereoisomers).

Provenance & Evidence