Potassium Carbonate → HCID 178517846, Verbindung

HRID 51308

Reaktionsgleichung

Reaktionsgleichung von HRID 51308
[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

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 669533-MorpholinoneHCID 9869224Ammonium cerium (IV) nitrateHCID 22289840Ethyl acetate methanol diethylamine

Produkt 1

HCID 178517846HCID 178517846, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

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+]

Aufarbeitung

  1. stirringthe mixture was stirred for 10 minutes
  2. customThe product was isolated by column chromatography on silica gel
  3. customwas further purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-1162d8b81ce0495ab8ba0da37aef36a3
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713496B2

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