Alternative method of Boc-removal from sulfamide using silica-phenyl sulfonic acid in conjunction with microwave heating.
A general method was used to prepare an array of unsymmetric sulfamides. This was accomplished by the stepwise addition of CSI to tert-butanol followed by the addition of amines. To increase diversity, nitrogen group of Boc-sulfamides was alkylated with alcohols using Mitsunobu reaction and Boc-group was removed using Si-TsOH. Microwave heating was used in all the steps. The final sulfamides were released from Si-TsOH using NH3 in MeOH.
Ghassemi
Shahnaz
S
Biotage, Charlottesville, Virginia, USA. sghassemi@biotage.com
Fuchs
Kristin
K
D000478:Alkylation; D001557:Benzenesulfonates / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D005563:Formic Acid Esters / Q000737:chemistry* / Q000302:isolation & purification*; D006358:Hot Temperature; D008872:Microwaves; D017640:Silicates / Q000737:chemistry*; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry*
D001557:Benzenesulfonates; D005563:Formic Acid Esters; D017640:Silicates; D013449:Sulfonamides; C508277:silica-phenylsulfonic acid; C000345:t-butyloxycarbonyl group