1-tert-Butyl 4-ethyl 5-oxoazepane-1,4-dicarboxylate → HCID 67979385, compound

HRID 528713Notes

Reaction equation

HRID 528713 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:12](=[O:13])[CH2:11][CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C1C=CC=CC=1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:12](=[O:13])[CH2:11][CH2:10][N:9]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 44365701-tert-Butyl 4-ethyl 5-oxoazepane-1,4-dicarboxylateHCID 178418268HCID 178418268, compound

Product 1

HCID 67979385HCID 67979385, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 241BenzeneSolvent

Procedure

To 4.64 g (16.26 mmol) 5-oxo-azepane-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (route 1 step a) in 200 mL benzene at room temperature was added 1.47 g (8.13 mmol) copper (II) acetate and the resulting reaction mixture was stirred at room temperature for 30 minutes. 7.21 g (16.26 mmol) lead (IV) tetraacetate was added and the reaction was stirred at room temperature for 3 hours. After evaporation of the solvent, the material was partitioned between 250 mL EtOAc and 150 mL H2O, the organic layer was separated and washed with H2O (150 mL) and saturated brine (150 mL) and dried over MgSO4. After filtration and evaporation of the solvent the resulting solid was used for the next step without further purification.

Workup

  1. customthe resulting reaction mixture
  2. stirringthe reaction was stirred at room temperature for 3 hours
  3. customAfter evaporation of the solvent
  4. customthe material was partitioned between 250 mL EtOAc and 150 mL H2O
  5. customthe organic layer was separated
  6. washwashed with H2O (150 mL) and saturated brine (150 mL)
  7. dry with materialdried over MgSO4
  8. filtrationAfter filtration and evaporation of the solvent the resulting solid
  9. customwas used for the next step without further purification

Sources & evidence

ORD record
ord-65aa2195e4234d46bfe8b53af75cc179
Source dataset
uspto-grants-2016_05
Patent number
US09346816B2

Reaction notes

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