反应详情

This amide was treated with Dess-Martin periodinane (114 mg, 0.153 mmol) at room temperature. After stirring for 1 hour, 5 mls 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 17 mg of N-[1-(5-Methoxymethyl-[1,3,4]oxadiazole-2-carbonyl)-propyl]-4-oxo-2-benzylsulfonylmethyl-4-pyrrolidin-1-yl-butyramide; H1 NMR(CDCl3): 8.2, 8(1H, d,d, NH, diastereomeric), 7.6–7.2(5H, m), 5.3–5.1(1H, m), 4.6(2H, s, OCH2), 4.3–4.1(3H, m), 3.8–3.2(9H, m), 3–2.4(2H, m), 2.2–1.4(6H, m), 0.95(3H, t); MS:519.6(M−1), 521.6(M+1).

1. waitAfter a further 0.5 hours
2. extractionthe reaction mixture was extracted with ethyl acetate
3. washwashed with brine
4. dry with materialdried with MgSO4
5. concentrationconcentrated
6. customThe residue was purified with silica gel column chromatography