Triacetoxyperiodinane → Benzyl {1-(4-bromobenzyl)-2-[(4,4-dimethyl-2-oxohexyl)amino]-2-oxoethyl}carbamate

HRID 425377Notes

Reaction equation

HRID 425377 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Br:23][C:24]1[CH:54]=[CH:53][C:27]([CH2:28][CH:29]([NH:42][C:43](=[O:52])[O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:30]([NH:32][CH2:33][CH:34]([OH:41])[CH2:35][C:36]([CH3:40])([CH3:39])[CH2:37][CH3:38])=[O:31])=[CH:26][CH:25]=1>C(Cl)Cl>[Br:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:28][CH:29]([NH:42][C:43](=[O:52])[O:44][CH2:45][C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:30]([NH:32][CH2:33][C:34](=[O:41])[CH2:35][C:36]([CH3:39])([CH3:40])[CH2:37][CH3:38])=[O:31])=[CH:53][CH:54]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86637795Benzyl {1-(4-bromobenzyl)-2-[(2-hydroxy-4,4-dimethylhexyl)amino]-2-oxoethyl}carbamate

Product 1

HCID 86637796Benzyl {1-(4-bromobenzyl)-2-[(4,4-dimethyl-2-oxohexyl)amino]-2-oxoethyl}carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (8.01 g, 18.9 mmol) was added to an ambient temperature solution of benzyl {1-(4-bromobenzyl)-2-[(2-hydroxy-4,4-dimethylhexyl)amino]-2-oxoethyl}carbamate (6.35 g, 12.6 mmol) in methylene chloride (200 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% ethyl acetate/hexane afforded benzyl {1-(4-bromobenzyl)-2-[(4,4-dimethyl-2-oxohexyl)amino]-2-oxoethyl}carbamate.

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-b33f8ff1788648039ac03f7736b3cd33
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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