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

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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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Authors and Affiliations

  1. Department of Pharmaceutical Sciences, Biomanufacturing Research Institute and Technology Enterprise (BRITE), North Carolina Central University, Durham, NC, 27707, USA

    Alfred L. Williams, Srinivasa R. Dandepally & Sharadsrikar V. Kotturi

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  1. Alfred L. Williams
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  2. Srinivasa R. Dandepally
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  3. Sharadsrikar V. Kotturi
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Correspondence to Alfred L. Williams.

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Williams, A.L., Dandepally, S.R. & Kotturi, S.V. A p-methoxybenzyl (PMB) protection/deprotection approach toward the synthesis of 5-phenoxy-4-chloro-N-(aryl/alkyl) thiophene-2-sulfonamides. Mol Divers 14, 697–707 (2010). https://doi.org/10.1007/s11030-009-9208-y

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