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

[Display omitted] 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 acti...

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Bibliographic Details
Published in:Tetrahedron letters 2022-04, Vol.96, p.153758, Article 153758
Main Authors: Faucon, Aline L., Hoegy, Françoise, Werle, Noémie, Gourlaouen, Christophe, Mislin, Gaëtan L.A.
Format: Article
Language:English
Subjects:
2,2′-Dipyridylamine
Amine protecting group
Chemical Sciences
Hydrolysis
t-Butylester
t-Butyloxycarbonyl
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Summary:[Display omitted] 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2022.153758