Isotope labeled ‘HEA/HEE’ moiety in the synthesis of labeled HIV‐protease inhibitors—Part II

[ 2 H 5 ]‐Amprenavir and [ 2 H 5 ]‐saquinavir have been prepared from a common labeled precursor (1S, 2S)‐(1‐oxiranyl‐2‐[ 2 H 5 ]phenylethyl)‐carbamic acid tert‐ butyl ester, 1 . Both of these compounds are in the ‘HEA’ class of HIV protease inhibitors. [ 2 H 5 ]‐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‐[ 2 H 5 ]phenylpropan‐1‐one, 11 , provided the [phenyl‐ 2 H 5 ]‐HEE core structure for synthesis of the desired labeled compound. Copyright © 2005 John Wiley & Sons, Ltd.