Question

What is the stable pH of the amine protecting groups Boc, Fmoc, and CBZ?​

Answer 1

Answer:

9-Fluorenylmethyl carbamate, FMOC amino, FMOC amine, FMOC amide

H2O: pH < 1, 100°C pH = 1, RT pH = 4, RT pH = 9, RT pH = 12, RT pH > 12, 100°C

Bases: LDA NEt3, Py t-BuOK Others: DCC SOCl2

Nucleophiles: RLi RMgX RCuLi Enolates NH3, RNH2 NaOCH3

Electrophiles: RCOCl RCHO CH3I Others: :CCl2 Bu3SnH

Reduction: H2 / Ni H2 / Rh Zn / HCl Na / NH3 LiAlH4 NaBH4

Oxidation: KMnO4 OsO4 CrO3 / Py RCOOOH I2, Br2, Cl2 MnO2/CH2Cl2