Reaction #5488

ord-dcb68cc3bff744d997cc097884f62d34

Reaction equation

CCOC(=O)[C@@H]1CCCCCC[C@H](Br)C(=O)N1
Cis ethyl 3-bromo-2-oxo-1-azacyclodecane-10-carboxylate
→
CCOC(=O)[C@@H]1CCCCCC[C@H](OC(C)=O)C(=O)N1
cis ethyl 3-acetoxy-2-oxo-1-azacyclodecane-10-carboxylate

Reactants

CCOC(=O)[C@@H]1CCCCCC[C@H](Br)C(=O)N1
Cis ethyl 3-bromo-2-oxo-1-azacyclodecane-10-carboxylate

Reagents

CC(=O)[O-].[Ag+]
Silver acetate

Solvents

CN(C)C=O
dimethylformamide
CCOC(C)=O
ethyl acetate

Conditions

Temperature
100°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureAfter cooling back to room temperature
  2. 2
    Filtrationfiltered through a pad of silica gel
  3. 3
    Otherthe solvent is evaporated

Procedure

Cis ethyl 3-bromo-2-oxo-1-azacyclodecane-10-carboxylate (2.96 g, 9.67 mmol) is dissolved in dimethylformamide (30 mL). Silver acetate (6.35 g, 38 mmol) is added, and the reaction is heated to 100° C. for 3 hours. After cooling back to room temperature, the reaction is diluted with ethyl acetate (100 mL), filtered through a pad of silica gel, and the solvent is evaporated to give crude cis ethyl 3-acetoxy-2-oxo-1-azacyclodecane-10-carboxylate.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05244889uspto-grants-1993_09