Triacetoxyperiodinane → HCID 10256500, compound

Participants

Reaction Steps

To a solution of N-[(S)-1-(Benzoxazol-2-yl-hydroxy-methyl)-butyl]-2-(1-benzyl-cyclopropylmethyl)-4-morpholin-4-yl-4-oxo-butyramide (55 mg, 0.103 mmol) in dry dichloromethane under N2 was added a solution of Dess-Martin Periodinane solution in dichloromethane (15% wt in DCM, 0.206 mmol) and stirred at room temperature for 1 hr. The mixture was quenched with a solution Na2SO3 (65.4 mg) in saturated NaHCO3 (20 mL). The aqueous layer was extracted with dichloromethane (2×25 mL). Organic extracts dried (MgSO4) and concentrated under reduced pressure. Residue purified by silica gel column chromatography eluting with a mixture of ethyl acetate and heptane (1:1 then 2:1) to give N-[(S)-1-(Benzoxazole-2-carbonyl)-butyl]-2-(1-benzyl-cyclopropylmethyl)-4-morpholin-4-yl-4-oxo-butyramide as white solid (43 mg).

Provenance & Evidence