Tetrahedron letters2022，Vol.964.DOI:10.1016/j.tetlet.2022.153758

Dipyridylamine-acetamide (Dpaa): A primary amine protecting group orthogonally cleavable under acidic conditions in the presence of t-butyloxycarbonyl (Boc) and t-butylester

Gourlaouen, Christophe Mislin, Gaetan L. A. Faucon, Aline L. Hoegy, Francoise Werle, Noemie
Tetrahedron letters2022，Vol.964.DOI:10.1016/j.tetlet.2022.153758
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  • NSTL
  • Elsevier

Dipyridylamine-acetamide (Dpaa): A primary amine protecting group orthogonally cleavable under acidic conditions in the presence of t-butyloxycarbonyl (Boc) and t-butylester

Gourlaouen, Christophe 1Mislin, Gaetan L. A. 2Faucon, Aline L. 2Hoegy, Francoise 2Werle, Noemie2
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作者信息

  • 1. Univ Strasbourg
  • 2. CNRS
  • 折叠

Abstract

We show that dipyridylamine-acetamide (Dpaa), can be cleaved under mild acidic conditions (30% formic acid in dichloromethane). The release of the amine function is orthogonal to other acid-labile protecting groups. Calculations suggest that the ease of Dpaa cleavage relies on activation of the carbonyl function by the protonated dipyridylamine nitrogen and activation of a water molecule by a hydrogen-bond network. (c) 2022 Elsevier Ltd. All rights reserved.

Key words

2 0-Dipyridylamine/Amine protecting group/Hydrolysis/t -Butyloxycarbonyl/t -Butylester

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出版年

2022
Tetrahedron letters

Tetrahedron letters

CCR
ISSN：0040-4039
参考文献量9
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