Description
Bis(2,4-dinitrophenyl)carbonate is used in the preparation of azapeptides.
Uses
Peptide and azapeptide coupling reagent that functions by activating amines, forming derivatives suitable for condensation with N-protected amino acids; converts carboxylic acids to activated esters.
Synthesis
Diphenyl carbonate (20 g) is added to a stirred mixture of conc HNO3 (100 mL) and conc H2SO4 (120 mL) at 50-55 °C over 1 h. The resulting suspension is stirred at 50 °C for 3 h, left at rt for 90 h and poured onto ice. The precipitate is washed with iced water and dried in vacuo over P2O5. This affords bis(2,4-dinitrophenyl) carbonate (31.2 g, 85%) which recrystallizes from hexane/benzene giving crystals, mp 144-146 °C.
Precautions
Store in a cool dry place to preclude contact with moisture; the hazardous and toxicological properties have not been investigated; may explode if heated rapidly
