Application of Odorless Thiols for the Cleavage of 2‐ and 4‐Nitrobenzenesulfonamides

Abstract

Several odorless or faint‐smelling thiols were tested to cleave 2‐ and 4‐nitrobenzenesulfonyl groups, which are widely utilized for selective protection and activation of amines. p‐Mercaptobenzoic acid (7) was found to be the most useful thiol for cleaving the o‐ and p‐nosyl groups in terms of ease of separation of the product from the workup residue, reaction temperature, and reaction time.

Keywords:

• Deprotection
• 2‐ and 4‐nitrobenzenesulfonamides
• odorless thiol

Acknowledgments

This research was financially supported in part by the Frontier Research Program and the 21st Century Center of Excellence Program “Development of Drug Discovery Frontier Integrated from Tradition to Proteome” of the Ministry of Education, Culture, Science, Sports, and Technology, Japan.