A p-methoxybenzyl (PMB) protection/deprotection approach toward the synthesis of 5-phenoxy-4-chloro-N-(aryl/alkyl) thiophene-2-sulfonamides.

Autor: Williams AL; Department of Pharmaceutical Sciences, Biomanufacturing Research Institute and Technology Enterprise (BRITE), North Carolina Central University, Durham, NC 27707, USA. awilliams@nccu.edu, Dandepally SR, Kotturi SV
Jazyk: angličtina
Zdroj: Molecular diversity [Mol Divers] 2010 Nov; Vol. 14 (4), pp. 697-707. Date of Electronic Publication: 2009 Nov 21.
DOI: 10.1007/s11030-009-9208-y
Abstrakt: The synthesis of 17 phenoxy substituted 4-chloro-N-(aryl/alkyl)thiophene-2-sulfonamides using a PMB protection/deprotection strategy is described. Nucleophilic displacement of p-methoxybenzyl (PMB) protected 4,5-dichloro-N-(aryl/alkyl)-thiophene-2-sulfonamides was carried out with different phenols under mild basic conditions. Reaction times of 3-6 h and overall yields of 78-98% were achieved with the PMB group in place compared to no reaction without this protecting group. The PMB group was easily and selectively removed in 68-98% yield using TFA in DCM.
Databáze: MEDLINE