NaBH4 - A novel method for the deprotection of Nω-nitro-arginine

Mónika Sebestyén, György Kóczán, A. Csámpai, F. Hudecz

Research output: Article

1 Citation (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)546-548
Number of pages3
JournalTetrahedron Letters
Volume57
Issue number5
DOIs
Publication statusPublished - febr. 3 2016

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ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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