Ceric ammonium nitrate → HCID 58716565, compound

HRID 1245229Notes

Reaction equation

HRID 1245229 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:25]=[N:26][CH:27]=[CH:28][CH:29]=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:25]=[N:26][CH:27]=[CH:28][CH:29]=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 58716562HCID 58716562, compound

Product 1

HCID 58716565HCID 58716565, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

(S)-N-[3-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(3-pyridyl)benzoyl]-1-phenylethylamine (69 mg, 0.1311 mmol) was dissolved in a mixed solvent of acetonitrile (9 ml) and water (3 ml), then CAN (180 mg, 0.3284 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 (48 mg, 0.0967 mmol, 74%).

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-b76ec1a6d42c400b888fb38a572e4e18
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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