反应详情

To a solution of morpholine-4-carboxylic acid (2-cyclopropylmethanesulfonyl-1-{1-[hydroxy-(5-phenyl-1,2,4-oxadiazol-3-yl)-methyl]-propylcarbamoyl}-ethyl)-amide (183 mg, 0.34 mmol) in methylene chloride (10 mL), Dess-Martin Periodinane (200 mg, 0.47 mmol) was added and stirred at room temperature for 2 hours. The reaction mixture was washed with a solution of Na2S2O3 in water (0.26M), saturated bicarbonate, and water, dried over Na2SO4 and concentrated under reduced pressure. The residue was subjected to flash chromatography eluting with a mixture of ethyl acetate and heptane to give morpholine-4-carboxylic acid {2-cyclopropylmethanesulfonyl-1-[1-(5-phenyl-1,2,4-oxadiazole-3-carbonyl)-propylcarbamoyl]-ethyl}-amide, a mixture of diastereomers, (45 mg) as an off white solid. 1H NMR (CDCl3): 8.22 (d, J=7 Hz, 2H), 7.83, 7.75 (2×d, J=7 Hz, 1H), 7.65 (m, 1H), 7.60–7.51 (m, 2H), 6.10–6.07 (2×d, J=7 Hz, 1H), 5.36 (m, 1H), 5.00–4.86 (m, 1H), 3.79 (I, 1H), 3.74–3.66 (m, 4H), 3.48 (m, 1H), 3.47–3.37 (m, 4H), 3.20–3.07 (m, 2H), 2.24–2.06 (m, 1H), 2.00–1.82 (m, 1H), 1.22 (m, 1H), 1.01 (t, J=7 Hz, 3H), 0.80–0.68 (m, 2H), 0.56–0.38 (m, 2H). MS: 534 (MH+).

1. washThe reaction mixture was washed with a solution of Na2S2O3 in water (0.26M), saturated bicarbonate, and water
2. dry with materialdried over Na2SO4
3. concentrationconcentrated under reduced pressure
4. washeluting with a mixture of ethyl acetate and heptane