Isotope Labeled 'Hea/Hee' Moiety In The Synthesis Of Labeled Hiv-Protease Inhibitors - Part Ii

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