American Chemical Society

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5‑Chloro-8-nitro-1-naphthoyl (NNap): A Selective Protective Group for Amines and Amino Acids

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journal contribution
posted on 2023-05-26, 13:10 authored by Asmaa Habib, José J. Garrido-González, Estela Sánchez-Santos, Irene Boya del Teso, Francisca Sanz, Victoria Alcázar, Ángel L. Fuentes de Arriba, Joaquín R. Morán
The synthesis of 5-chloro-8-nitro-1-naphthoyl chloride and its use as a protective group for amines is described. Protection is carried out with an auxiliary amine or under mild Schotten-Baumann conditions in high yield (>86%), while deprotection can be achieved easily under gentle reducing conditions due to the large steric tension between C-1 and C-8 naphthalene substituents. The reaction has been successfully tested in dipeptide synthesis and amino alcohols protection, and it has proved selective for the ε-amine group of lysine.