Potassium Carbonate → HCID 178517846, compound

HRID 968437

Reaction equation

HRID 968437 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

HCID 178517846HCID 178517846, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

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+]

Workup

  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

Sources & evidence

ORD record
ord-f07fff6300404df58f97c65d192a3edb
Source dataset
uspto-grants-2005_10
Patent number
US06958402B2

Linked notes

Loading…