Triacetoxyperiodinane → n-(2-Benzooxazol-2-yl-1-methoxymethyl-2-oxo-ethyl)-2-(2-difluoromethoxy-benzylsulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyramide

Participants

Reaction Steps

This amide (150 mg, 0.24 mmol) was treated with Dess-Martin periodinane (178 mg, 0.36 mmol) at room temperature. After stirring for 1 hour, 5 ml of saturated Na2S2O3—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 39 mg of N-(2-Benzooxazol-2-yl-1-methoxymethyl-2-oxo-ethyl)-2-(2-difluoromethoxy-benzylsulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyramide; H1 NMR(DMSO-d): 8.97, 8.8(1H, dd, J=5.6 Hz, J=5.6 Hz, NH, diastereomeric), 8.02–7.94(1H, m), 7.9–7.84(1H, m), 7.66–7.58(1H, m), 7.55–7.38(3H, m), 7.3–7.18(2H, m), 7.1(1H, t, J=73.6 Hz), 5.54–5.42(1H, m), 4.6–4.4(4H, m), 3.92–3.84(1H, m), 3.82–3.72(1H, m), 3.68–3.1(11H, m), 2.7–2.56(1H, m), 1.7–1.55(1H, m), 1.3–1(1H, m); MS: 622.4(M−1), 624.3(M+1), 646.3(M+Na).

Provenance & Evidence