Formamide

Formamide scheme

Protection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • HCO2Et Et3N
    N/A
    Reflux
    ON
    92 %
    intermediate structure
    HCO2Et
    Et3N
    Reflux, ON, 92%
    intermediate structure
  • HCO2Ph
    EtOAc
    Reflux
    45 min
    94 %
    intermediate structure
    HCO2Ph
    EtOAc
    Reflux, 45 min, 94%
    intermediate structure
  • HCO2Ac
    HCO2H
    RT - 50 °C
    30 min - 12 h
    90 - 95 %
    intermediate structure
    HCO2Ac
    HCO2H
    RT to 50 °C, 30 min, 95%
    intermediate structure
    intermediate structure
    HCO2Ac
    HCO2H
    RT, 12 h, 90%
    intermediate structure

Deprotection :

  • Reagents
    Solvents
    Temperature
    Time
    Yield
  • HCl
    MeOH H2O
    Reflux
    18 h
    98 %
    intermediate structure
    HCl
    MeOH, H2O
    Reflux, 18 h, 98%
    intermediate structure
  • HCl
    Acetone H2O
    Reflux
    60 min
    79 %
    intermediate structure
    HCl
    Acetone, H2O
    Reflux, 60 min, 79%
    intermediate structure
  • NaOH
    MeOH
    RT
    20 h
    80 %
    intermediate structure
    NaOH
    MeOH
    RT, 20 h, 80%
    intermediate structure