Selective Protection of Secondary Amines as the N-Phenyltriazenes. Application to Aminoglycoside Antibiotics.

Selective protection of secondary amines as triazenes in the presence of multiple primary amines is demonstrated, with subsequent protection of the primary amines as either azides or carbamates in the same pot. Aminoglycoside antibiotic examples reveal broad functional group compatibility. The triazene group is removed with trifluoroacetic acid and, because of the low barrier to rotation, affords sharp (1)H NMR spectra at room temperature.