Triacetoxyperiodinane → 2-Cyclohexylmethyl-n-[1-(5-ethyl-[1,3,4]oxadiazole-2-carbonyl)-butyl]-4-morpholin-4-yl-4-oxo-butyramide

Participants

Reaction Steps

This amide was treated with Dess-Martin periodinane (239 mg, 0.48 mmol) at room temperature. After stiffing for 1 hour, 5 mls of saturated Na2SO3—NaHCO3 were added. After a further 0.5 hours, the reaction mixture was extracted with ethyl acetate, washed with brine, dried with MgSO4 and concentrated. The residue was purified with silica gel column chromatography to yield 65 mg of 2-cyclohexylmethyl-N-[1-(5-ethyl-[1,3,4]oxadiazole-2-carbonyl)-butyl]-4-morpholin-4-yl-4-oxo-butyramide; H1 NMR (DMSO-d): 8.6, 8.51(11H, dd, J=6.8 Hz, J=5.6 Hz, NH, diastereomeric), 4.98(−4.88 (1H, m), 3.6–3.25(8H, m), 3–2.9(2H, q, J=7.6 Hz), 2.9–2.75(1H, m), 2.5–2.4(1H, m), 2.3–2.1(1H, m), 1.9–1.7(2H, m), 1.7–1.4(7H, m), 1.4–1.2(2H, m), 1.28(3H, t), 1.2–1(6H, m), 0.88(3H, t); MS: 461.4(M−1), 463.4(M+1), 485.4(M+Na).

Provenance & Evidence