(NNap): A Selective
Protective Group for Amines and Amino Acids
Posted on 2023-05-26 - 13:10
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.
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Habib, Asmaa; Garrido-González, José J.; Sánchez-Santos, Estela; del Teso, Irene Boya; Sanz, Francisca; Alcázar, Victoria; et al. (2023): 5‑Chloro-8-nitro-1-naphthoyl (NNap): A Selective Protective Group for Amines and Amino Acids. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.3c01334
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José J. Garrido-González
Irene Boya del Teso
Ángel L. Fuentes de Arriba
Joaquín R. Morán