Ceric ammonium nitrate → HCID 58716567, compound

HRID 1245231Notes

Reaction equation

HRID 1245231 reaction equation
C[O:2][C:3]1[C:4]([CH3:39])=[C:5]([C:30]([O:37]C)=[C:31]([O:35][CH3:36])[C:32]=1[O:33][CH3:34])[CH2:6][C:7]1[C:8]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)=[C:9]([CH:21]=[CH:22][CH:23]=1)[C:10]([NH:12][C@H:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14])=[O:11].O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].C(=O)([O-])O.[Na+]>C(#N)C.O>[CH3:34][O:33][C:32]1[C:3](=[O:2])[C:4]([CH3:39])=[C:5]([CH2:6][C:7]2[C:8]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)=[C:9]([CH:21]=[CH:22][CH:23]=2)[C:10]([NH:12][C@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])=[O:11])[C:30](=[O:37])[C:31]=1[O:35][CH3:36]

Participants

6

Reactant 3

HCID 180504Ceric ammonium nitrateHCID 516892Sodium BicarbonateHCID 58716568HCID 58716568, compound

Product 1

HCID 58716567HCID 58716567, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

(S)-N-[3-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoyl]-1-phenylethylamine (64 mg, 0.1216 mmol) was dissolved in a mixed solvent of acetonitrile (9 ml) and water (3 ml), then CAN (166 mg, 0.3029 mmol) was added thereto at room temperature and the mixture was stirred for 3 hours. The reaction solution was poured into water, neutralized with a saturated aqueous solution of sodium hydrogen carbonate and extracted with ethyl acetate. The extract was washed with water and dried and the solvent was evaporated therefrom. The residue was purified by preparative thin layer silica gel (hexane:ethyl acetate=1:3) to give the title compound (30 mg, 0.0604 mmol, 50%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was evaporated
  5. customThe residue was purified by preparative thin layer silica gel (hexane:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-5e9d78271e4c4f0d8e7562153be10174
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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