NaBH4 – a novel method for the deprotection of Nω-nitro-arginine

[Display omitted] The selective deprotection of Nω-nitro-arginine derivatives represents a major preparative challenge. This problem can be circumvented by the use of catalytic hydrogenation, but often high pressure, elevated temperature, and/or long reaction times are needed. In certain cases hydro...

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Bibliographic Details
Published in:Tetrahedron letters 2016-02, Vol.57 (5), p.546-548
Main Authors: Sebestyén, Mónika, Kóczán, György, Csámpai, Antal, Hudecz, Ferenc
Format: Article
Language:English
Subjects:
Catalyst
Nω-Nitro–Arg deprotection
Selective removal
Sodium borohydride
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Summary:[Display omitted] The selective deprotection of Nω-nitro-arginine derivatives represents a major preparative challenge. This problem can be circumvented by the use of catalytic hydrogenation, but often high pressure, elevated temperature, and/or long reaction times are needed. In certain cases hydrogenation is not suitable, for example, small-scale reactions, parallel synthesis, or due to selectivity issues. Herein, we demonstrate for the first time, the use of NaBH4 in the presence of a metal ion catalyst for the removal of the Nω-nitro moiety under simple, ‘open-vessel’ conditions. This process using NaBH4 does not remove the benzyloxycarbonyl-protecting group; thus the method is orthogonal for this protecting scheme.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.12.081