Synthesis of p-amino-N,N′-dihydroxybenzamidine using a TBDMS protecting group protocol |
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Authors: | Laura Schwarz Ulrich GirreserBernd Clement |
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Affiliation: | Pharmaceutical Institute, Department of Pharmaceutical and Medicinal Chemistry, Christian-Albrechts-University of Kiel, Gutenbergstraße 76, 24118 Kiel, Germany |
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Abstract: | A synthetic route to p-amino-N,N′-dihydroxybenzamidine is established using a TBDMS protecting group strategy starting with p-nitrobenzhydroxamic acid chloride, which is transformed to O,O′-bis(tert-butyldimethylsilyl)-N,N′-dihydroxybenzamidine. Reduction with sodium dithionite occurs without degradation of the dihydroxyamidine functional group. Deprotection with ammonium fluoride is fast and efficient. This is important because no other possibility to synthesize this derivative has been found up to now. Furthermore, TBDMS protecting group strategy is proved to be adaptable to other substituted N,N′-dihydroxybenzamidines. |
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Keywords: | Silyl ether Prodrugs Protective groups Amidines Synthesis |
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