Fast, efficient and selective deprotection of the tert-butoxycarbonyl (Boc) group using HCl/dioxane (4 m).
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 Nalpha-Boc groups in the presence of tert-butyl esters and tert-butyl ethers, including thio-tert-butyl ethers, but not phenolic tert-butyl ethers.
Han
G
G
Department of Chemistry, University of Arizona, Tucson, AZ 85721, USA.
Tamaki
M
M
Hruby
V J
VJ
D004146:Dioxanes / Q000737:chemistry*; D005563:Formic Acid Esters / Q000737:chemistry*; D006851:Hydrochloric Acid / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis*
D004146:Dioxanes; D005563:Formic Acid Esters; D007202:Indicators and Reagents; D010455:Peptides; C000345:t-butyloxycarbonyl group; C025223:1,4-dioxane; D006851:Hydrochloric Acid