Amide-Assisted Hydrolysis of β-Carboxamido-Substituted Phosphinic Acid Esters
- 1 May 1997
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 62 (9) , 2808-2812
- https://doi.org/10.1021/jo962275w
Abstract
Phosphinic acids are of interest due to their ability to inhibit metalloproteases. The hydrolysis of a phosphinic acid ester is typically one of the final steps in the synthesis of such inhibitors. We have found that the acid-catalyzed hydrolysis of a phosphinic acid ester containing a beta-carboxamido group is facilitated by the presence of the amide. The promotion of the hydrolysis is dependent on the electron density of the amide suggesting the intermediacy of a cyclic imidate structure (C). The hydrolysis of phosphinic acid esters containing a beta-carboxamido group is conveniently and quantitatively effected by treating the ester with 10:90 H(2)O:TFA.Keywords
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