[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][C:2]1=[O:7].[N+]([O-])([O-])=O.[Ce+4].[NH4+:13].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.C(=O)([O-])[O-].[K+].[K+].C(O[CH2:40][CH3:41])(=O)C.CO.[CH2:44]([NH:46][CH2:47]C)C>O.C(#N)C>[NH:46]1[CH:47]=[C:40]([CH2:41][C@@H:3]2[O:4][CH2:5][CH2:6][NH:1][C:2]2=[O:7])[N:13]=[CH:44]1
A mixture of the protected morpholinone of Preparation 53 (500 mg, 1.66 mmol), and ammonium cerium (IV) nitrate (2.5 g, 4.5 mmol) in water (6 ml) and acetonitrile (6 ml) was stirred at 40° C. for 18 hours. Potassium carbonate (1.5 g) was added and the mixture was stirred for 10 minutes then adsorbed onto silica gel. The product was isolated by column chromatography on silica gel using ethyl acetate:methanol:diethylamine (96:2:2 to 80:10:10) and was further purified by column chromatography on silica gel using dichloromethane:methanol (90:10 to 85:15) to afford the title compound, 240 mg. 1H-NMR (CD3OD, 400 MHz) δ: □3.02-3.42 (m, 4H), 3.78 (m, 1H0, 4.00 (m, 1H), 4.38 (m, 1H), 6.75 (s, 1H), 7.78 (s, 1H). HRMS: m/z (ES+) 182.0924 [MH+]
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