Fast, efficient and selective deprotection of the tert-butoxycarbonyl (Boc) group using HCL/dioxane (4 M)

G. Han, M. Tamaki, V. J. Hruby*

*Corresponding author for this work

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128 Citations (Scopus)

Abstract

Fast, efficient and selective deprotection of the tert-butoxycarbonyl (Boc) group of various amino acids and peptides was achieved by using hydrogen chloride (4 M) in anhydrous dioxane solution for 30 min at room temperature. In the cases studied in our laboratory, this protocol provided superior selectivity to deprotect Nα-Boc groups in the presence of tert-butyl esters and tert-butyl ethers, including thio-tert-butyl ethers, but not phenolic tert-butyl ethers.

Original languageEnglish
Pages (from-to)338-341
Number of pages4
JournalJournal of Peptide Research
Volume58
Issue number4
DOIs
Publication statusPublished - 2001
Externally publishedYes

Keywords

  • Boc
  • Dioxane
  • Hydrogen chloride
  • Selective deprotection
  • Tert-butyl ester

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