Ceric ammonium nitrate → HCID 42599869, compound

HRID 1898738Notes

Reaction equation

HRID 1898738 reaction equation
[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][NH:5][C:6]([C:8]1([CH3:22])[CH2:17][CH2:16][C:15]2[C:10](=[C:11]([CH3:21])[C:12]([CH3:20])=[C:13]([OH:19])[C:14]=2[CH3:18])[O:9]1)=[O:7].[O:24]=[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+]>>[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][NH:5][C:6](=[O:7])[C:8]([OH:24])([CH3:22])[CH2:17][CH2:16][C:15]1[C:10](=[O:9])[C:11]([CH3:21])=[C:12]([CH3:20])[C:13](=[O:19])[C:14]=1[CH3:18]

Participants

4

Reactant 3

HCID 180504Ceric ammonium nitrateHCID 516892Sodium BicarbonateHCID 11723535HCID 11723535, compound

Product 1

HCID 42599869HCID 42599869, compoundYield 83.2%

Procedure

Oxidation as described in protocol B, using 150 mg N-(2-(dimethylamino)-ethyl)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxamide (0.468 mmol) and 564 mg CAN (1.03 mmol) with exceptions as noted. The aqueous phase was basified with NaHCO3 (s), extracted with EtOAc and the combined organics dried with Na2SO4, concentrated and flashed yielding 131 mg (83%) of N-(2-(dimethylamino)-ethyl)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide as a yellow solid.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialthe combined organics dried with Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-30cad7f83d7a49b99f5599e9f226e976
Source dataset
uspto-grants-2013_08
Patent number
US08519001B2

Reaction notes

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