Solid-Phase Synthesis of an Oxalic Acid Amide Library
- 16 January 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Combinatorial Chemistry
- Vol. 6 (2) , 224-229
- https://doi.org/10.1021/cc030012r
Abstract
Monoamides of oxalic acid are of interest as bioisosteric replacements for phosphate groups in the design of new enzyme inhibitors. Here, we have demonstrated the use of oxalic acid as a linker to the Wang resin to synthesize individual or libraries of phosphate biosteres. The highly reactive resin-bound acid chloride reacts with arylamines to yield resin-bound N-aryloxamic acids (oxanilic acids). This methodology is especially useful for the rapid synthesis of 2-(oxalylamino)benzoic acids (OBAs), because it can be utilized for library synthesis and eliminates the intermediate purification step necessary in solution-phase reactions. The products are cleaved off the resin with trifluoroacetic acid in dichloromethane in good yields.Keywords
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