A <Emphasis Type="Italic">p</Emphasis>-methoxybenzyl (PMB) protection/deprotection approach toward the synthesis of 5-phenoxy-4-chloro-<Emphasis Type="Italic">N</Emphasis>-(aryl/alkyl) thiophene-2-sulfonamides |
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| Authors: | Alfred L Williams Srinivasa R Dandepally and Sharadsrikar V Kotturi |
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| Institution: | (1) Department of Pharmaceutical Sciences, Biomanufacturing Research Institute and Technology Enterprise (BRITE), North Carolina Central University, Durham, NC 27707, USA |
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| Abstract: | 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. |
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