tert-Butoxy carbamate (Boc)

tert-Butoxy carbamate (Boc) scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • Boc2O Et3N
    CH2Cl2
    RT
    60 min
    100 %
    intermediate structure
    Boc2O, Et3N
    CH2Cl2
    RT, 60 min, 100%
    intermediate structure
  • Boc2O NaHCO3
    EtOAc H2O
    RT
    3 h
    91 %
    intermediate structure
    Boc2O, NaHCO3
    EtOAc, H2O
    RT, 3 h, 91%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • CF3CO2H
    CH2Cl2
    0 °C - RT
    20 min - 6 h
    65-91 %
    intermediate structure
    CF3CO2H
    CH2Cl2
    RT, 20 min, 83%
    intermediate structure
    intermediate structure
    CF3CO2H
    CH2Cl2
    RT, 6 h, 65%
    intermediate structure
    intermediate structure
    CF3CO2H
    CH2Cl2
    RT, 60 min, 91%
    intermediate structure
    intermediate structure
    CF3CO2H
    CH2Cl2
    RT, 5 h, 89%
    intermediate structure
    intermediate structure
    CF3CO2H
    CH2Cl2
    0 °C to RT, 30 min, 90%
    intermediate structure
  • TMSOTf Et3N
    CH2Cl2
    0 °C - RT
    60 min
    97 %
    intermediate structure
    TMSOTf, Et3N
    CH2Cl2
    0 °C to RT, 60 min, 97%
    intermediate structure
  • AcCl
    EtOH
    RT
    16 h
    100 %
    intermediate structure
    AcCl
    EtOH
    RT, ON, 100%
    intermediate structure