Ethyl Acetate → HCID 42599387, compound

HRID 2428258Notes

Reaction equation

HRID 2428258 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10]([C:12]2([CH3:26])[CH2:21][CH2:20][C:19]3[C:14](=[C:15]([CH3:25])[C:16]([CH3:24])=[C:17]([OH:23])[C:18]=3[CH3:22])[O:13]2)=[O:11])[CH:5]=[CH:4][N:3]=[CH:2]1.[O:27]=[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+].CCOC(C)=O>C(C#N)(C)=O.C(Cl)Cl.O>[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:11])[C:12]([OH:27])([CH3:26])[CH2:21][CH2:20][C:19]2[C:14](=[O:13])[C:15]([CH3:25])=[C:16]([CH3:24])[C:17](=[O:23])[C:18]=2[CH3:22])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 180504Ceric ammonium nitrateHCID 67262909HCID 67262909, compound

Product 1

HCID 42599387HCID 42599387, compoundYield 93.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 694302-OxopropiononitrileSolvent

Procedure

To a solution of N-(3-(1H-imidazol-1-yl)propyl)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxamide (100.7 mg, 0.282 mmol) in 6 mL AcCN and 6 mL CH2Cl2, cooled to 0° C., was added a cooled solution of CAN (340 mg, 0.620 mmol) in 2 mL H2O, dropwise over 5 minutes. The reaction was immediately treated with 5 mL EtOAc and washed 3×3 mL H2O. The aqueous layer was basified with 6 mL saturated NaHCO3 solution and extracted 6×3 mL EtOAc. The combined organics were dried over Na2SO4 and concentrated to a yellow oil. Flash chromatography yielded 98.1 mg of N-(3-(1H-imidazol-1-yl)propyl)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide as a yellow solid.

Workup

  1. washwashed 3×3 mL H2O
  2. extractionextracted 6×3 mL EtOAc
  3. dry with materialThe combined organics were dried over Na2SO4
  4. concentrationconcentrated to a yellow oil

Sources & evidence

ORD record
ord-7af1f47b09b54aef987f13a980bfd0cc
Source dataset
uspto-grants-2011_06
Patent number
US07968746B2

Reaction notes

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