Triacetoxyperiodinane → 4-Acetylamino-5-oxo-azepane-1-carboxylic acid benzyl ester

HRID 239178Notes

Reaction equation

HRID 239178 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([O:30][C:31]([N:33]1[CH2:39][CH2:38][CH:37]([OH:40])[CH:36]([NH:41][C:42](=[O:44])[CH3:43])[CH2:35][CH2:34]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl>[CH2:23]([O:30][C:31]([N:33]1[CH2:39][CH2:38][C:37](=[O:40])[CH:36]([NH:41][C:42](=[O:44])[CH3:43])[CH2:35][CH2:34]1)=[O:32])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86686080HCID 86686080, compound

Product 1

HCID 866860824-Acetylamino-5-oxo-azepane-1-carboxylic acid benzyl esterYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

11 g Dess Martin Periodane was added to 6.2 g 4-acetylamino-5-hydroxy-azepane-1-carboxylic acid benzyl ester in 100 mL dichloromethane and stirred for 1 h at RT. The mixture was diluted with dichloromethane and washed with 2 mol/L sodium hydroxide solution. The organic layer was washed with brine, dried and concentrated. The residue was purified by chromatographie on silica gel (EtOAc) to yield 5.5 g of the desired product. (M+H)+: 305

Workup

  1. washwashed with 2 mol/L sodium hydroxide solution
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by chromatographie on silica gel (EtOAc)

Sources & evidence

ORD record
ord-ff30ce1aed3145a982de33c66e007520
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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