Triacetoxyperiodinane → 2-chloro-N-(4-(((2-oxo-1-phenylpropyl)amino)carbonyl)phenyl)benzamide

HRID 1951583Notes

Reaction equation

HRID 1951583 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([NH:15][CH:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]([OH:19])[CH3:18])=[O:14])=[CH:9][CH:8]=1)=[O:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]([NH:15][CH:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17](=[O:19])[CH3:18])=[O:14])=[CH:11][CH:12]=1)=[O:5]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 574653742-chloro-N-(4-(((2-hydroxy-1-phenylpropyl)amino)carbonyl)phenyl)benzamide

Product 1

HCID 574653752-chloro-N-(4-(((2-oxo-1-phenylpropyl)amino)carbonyl)phenyl)benzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

a mixture of 2-chloro-N-(4-(((2-hydroxy-1-phenylpropyl)amino) carbonyl)phenyl)benzamide (294 mg, 719 μmol) and Dess-Martin periodinane (335 mg, 791 μmol) in 5 mL dichloromethane+1 mL DMF was stirred at room temperature for 2 hours then diluted with 20 mL ethyl acetate and washed with 10 mL each water and brine. The organic layer was stirred over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to afford a yellow solid. The solid was slurried in hot ethyl acetate and left to equilibrate to room temperature. After 48 h, the solid was collected by filtration, rinsing with ethyl acetate and drying over a stream of air (200 mg, 68%). ESI+ m/z=407.0 [MH]+.

Workup

  1. washwashed with 10 mL each water and brine
  2. stirringThe organic layer was stirred over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customto afford a yellow solid
  6. waitleft
  7. customto equilibrate to room temperature
  8. waitAfter 48 h
  9. filtrationthe solid was collected by filtration
  10. washrinsing with ethyl acetate
  11. customdrying over a stream of air (200 mg, 68%)

Sources & evidence

ORD record
ord-dc2335b733584077b042e98bee9257cf
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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