Mild and selective sodium azide mediated cleavage of p-nitrobenzoic esters.
[reaction: see text] A mild and selective cleavage of p-nitrobenzoic esters by sodium azide in methanol is reported. This new methodology is mild enough for use with acid- or base-sensitive compounds. No elimination byproducts are formed. Fmoc- and trifluoroacetyl-amino protecting groups, benzyl esters, and ethyl esters remain unaffected. Less reactive compounds are discussed in terms of steric factors, and yields are increased by altering the azide solvation.
Gómez-Vidal
J A
JA
Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60201-3113, USA.
Forrester
M T
MT
Silverman
R B
RB
D000596:Amino Acids / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D007202:Indicators and Reagents; D009579:Nitrobenzoates / Q000737:chemistry*; D019810:Sodium Azide / Q000737:chemistry*
D000596:Amino Acids; D004952:Esters; D007202:Indicators and Reagents; D009579:Nitrobenzoates; D019810:Sodium Azide; C008629:4-nitrobenzoic acid