2-Nitrophenol → Nitrophenyl benzyl carbonate

Participants

Reaction Steps

To a stirring solution of 3′,4′,3′″,4′″-tetra-dehydro-3,2′,6′,2′″,6′″-penta-Cbz-neomycin (4, 190 mg, 0.156 mmol) in DMF (2 mL) was added succinimidyl benzoyloxy(2-Cbz-aminoethyl)carbamate (3, 81 mg, 0.18 mmol) and the reaction was stirred under a nitrogen atmosphere. DIPEA (67 μL, 0.38 mmol) was added and the reaction was stirred for 2 days. The reaction mixture was purified on a 2-inch reverse-phase HPLC column, followed by treatment with sat. aq. NaHCO3 to remove the benzoyl protecting group to yield a crude, which was purified on a 1-inch reverse-phase column to yield (5) (60 mg, 0.041 mmol, 26.3% yield): MS m/z (M+Na)+ calc. 1475.5, obs. 1475.4.

Provenance & Evidence