Dipyridylamine-acetamide (Dpaa): A primary amine protecting group orthogonally cleavable under acidic conditions in the presence of t-butyloxycarbonyl (Boc) and t-butylester - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Tetrahedron Letters Année : 2022

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

Résumé

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.

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hal-03795448 , version 1 (04-10-2022)

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Aline Faucon, Françoise Hoegy, Noémie Werle, Christophe Gourlaouen, Gaëtan L.A. Mislin. Dipyridylamine-acetamide (Dpaa): A primary amine protecting group orthogonally cleavable under acidic conditions in the presence of t-butyloxycarbonyl (Boc) and t-butylester. Tetrahedron Letters, 2022, 96, pp.153758. ⟨10.1016/j.tetlet.2022.153758⟩. ⟨hal-03795448⟩
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