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

[Image: see text] 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 gen...

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Autores principales: Habib, Asmaa, Garrido-González, José J., Sánchez-Santos, Estela, del Teso, Irene Boya, Sanz, Francisca, Alcázar, Victoria, Fuentes de Arriba, Ángel L., Morán, Joaquín R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10262267/
https://www.ncbi.nlm.nih.gov/pubmed/37232572
http://dx.doi.org/10.1021/acs.orglett.3c01334
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author Habib, Asmaa
Garrido-González, José J.
Sánchez-Santos, Estela
del Teso, Irene Boya
Sanz, Francisca
Alcázar, Victoria
Fuentes de Arriba, Ángel L.
Morán, Joaquín R.
author_facet Habib, Asmaa
Garrido-González, José J.
Sánchez-Santos, Estela
del Teso, Irene Boya
Sanz, Francisca
Alcázar, Victoria
Fuentes de Arriba, Ángel L.
Morán, Joaquín R.
author_sort Habib, Asmaa
collection PubMed
description [Image: see text] 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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spelling pubmed-102622672023-06-15 5-Chloro-8-nitro-1-naphthoyl (NNap): A Selective Protective Group for Amines and Amino Acids Habib, Asmaa Garrido-González, José J. Sánchez-Santos, Estela del Teso, Irene Boya Sanz, Francisca Alcázar, Victoria Fuentes de Arriba, Ángel L. Morán, Joaquín R. Org Lett [Image: see text] 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. American Chemical Society 2023-05-26 /pmc/articles/PMC10262267/ /pubmed/37232572 http://dx.doi.org/10.1021/acs.orglett.3c01334 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Habib, Asmaa
Garrido-González, José J.
Sánchez-Santos, Estela
del Teso, Irene Boya
Sanz, Francisca
Alcázar, Victoria
Fuentes de Arriba, Ángel L.
Morán, Joaquín R.
5-Chloro-8-nitro-1-naphthoyl (NNap): A Selective Protective Group for Amines and Amino Acids
title 5-Chloro-8-nitro-1-naphthoyl (NNap): A Selective Protective Group for Amines and Amino Acids
title_full 5-Chloro-8-nitro-1-naphthoyl (NNap): A Selective Protective Group for Amines and Amino Acids
title_fullStr 5-Chloro-8-nitro-1-naphthoyl (NNap): A Selective Protective Group for Amines and Amino Acids
title_full_unstemmed 5-Chloro-8-nitro-1-naphthoyl (NNap): A Selective Protective Group for Amines and Amino Acids
title_short 5-Chloro-8-nitro-1-naphthoyl (NNap): A Selective Protective Group for Amines and Amino Acids
title_sort 5-chloro-8-nitro-1-naphthoyl (nnap): a selective protective group for amines and amino acids
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10262267/
https://www.ncbi.nlm.nih.gov/pubmed/37232572
http://dx.doi.org/10.1021/acs.orglett.3c01334
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