Synthesis of Versatile N-Protected Amino Acid Esters from Aryl 4-Nitrosulfonates

Key words

coupling reagent - amino acid aryl esters - nitrophenyl nitrobenzenesulfonate - pentafluorophenyl nitrobenzenesulfonate

Significance

The development of easily accessible and novel coupling reagents for the synthesis of activated amino acid esters is an important aspect of peptide chemistry. In 1999, Pudhom and Vilaivan found that aryl 4-nitrosulfonates are highly efficient reagents for the synthesis of aryl esters of protected amino acids.

Comment

A series of 4-nitrophenyl or pentafluorophenyl esters of Boc- or Fmoc-protected amino acids were synthesized in good yield by treatment of amino acid with the corresponding aryl 4-nitrosulfonates in the presence of a base and a catalytic amount of 1-hydroxybenzotriazole (HOBt). This protocol is a beneficial and sustainable alternative to classical methods for the synthesis of activated aryl esters of protected amino acids.

Publication History

Article published online:
17 May 2022