Triacetoxyperiodinane → 2-(acetylamino)-3-(4-bromophenyl)-N-(4,4-dimethyl-2-oxohexyl)propanamide

HRID 425401Notes

Reaction equation

HRID 425401 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([NH:26][CH:27]([CH2:40][C:41]1[CH:46]=[CH:45][C:44]([Br:47])=[CH:43][CH:42]=1)[C:28]([NH:30][CH2:31][CH:32]([OH:39])[CH2:33][C:34]([CH3:38])([CH3:37])[CH2:35][CH3:36])=[O:29])(=[O:25])[CH3:24]>C(Cl)Cl>[C:23]([NH:26][CH:27]([CH2:40][C:41]1[CH:46]=[CH:45][C:44]([Br:47])=[CH:43][CH:42]=1)[C:28]([NH:30][CH2:31][C:32](=[O:39])[CH2:33][C:34]([CH3:37])([CH3:38])[CH2:35][CH3:36])=[O:29])(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 667058552-(acetylamino)-3-(4-bromophenyl)-N-(2-hydroxy-4,4-dimethylhexyl)propanamide

Product 1

HCID 667056452-(acetylamino)-3-(4-bromophenyl)-N-(4,4-dimethyl-2-oxohexyl)propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (2.94 g, 6.92 mmol) was added to an ambient temperature solution of 2-(acetylamino)-3-(4-bromophenyl)-N-(2-hydroxy-4,4-dimethylhexyl)propanamide (1.43 g, 3.46 mmol) in methylene chloride (100 mL). After stirring at ambient temperature for 2 h, the reaction mixture was quenched with saturated aqueous sodium thiosulfate/saturated aqueous sodium bicarbonate (1:1) and extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-80% acetone/methylene chloride afforded 2-(acetylamino)-3-(4-bromophenyl)-N-(4,4-dimethyl-2-oxohexyl)propanamide.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous sodium thiosulfate/saturated aqueous sodium bicarbonate (1:1)
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-342a1d942e514611a0eec910e4bb4815
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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