Isotope labeled ?HEA/HEE? moiety in the synthesis of labeled HIV-protease inhibitors?Part II

Abstract

[2H5]-Amprenavir and [2H 5]-saquinavir have been prepared from a common labeled precursor (1S, 2S)-(1-oxiranyl-2-[2H5]phenylethyl)-carbamic acid tert-butyl ester, 1. Both of these compounds are in the ‘HEA’ class of HIV protease inhibitors. [2H5]-Indinavir, a representative of the ‘HEE’ group of protease inhibitors, has also been synthesized. In the case of indinavir, 1S-(2,2-dimethyl-8, 8a-dihydro-3aH-indeno-[1,2-d]-oxazol-3R-yl)-2-oxiranylmethyl-3-[2H5]phenylpropan-1-one, 11, provided the [phenyl-2H5]-HEE core structure for synthesis of the desired labeled compound. Copyright © 2005 John Wiley & Sons, Ltd.