Synthesis of a Potent Cathepsin S Inhibitor Labeled with Deuterium and Carbon-14

Title:Synthesis of a Potent Cathepsin S Inhibitor Labeled with Deuterium and Carbon-14

Volume: 5 Issue: 4

Author(s): Bachir Latli, Matt Hrapchak, Jon C. Lorenz, Carl A. Busacca and Chris Senanayake

Affiliation:

Keywords: Cathepsin S, carbon-14, deuterium, radiosynthesis.

Abstract: Morpholine-4-carboxylic acid {(S)-1-[4-cyano-1-(3-morpholin-4-yl-propyl)-piperidin-4-ylcarbamoyl]-4,4- dimethyl-hexyl}-amide, (1) is a potent reversible and selective cathepsin S inhibitor. Deuterium labeled (1) was prepared in four steps in 62% overall yield from [2H8]- morpholine and chiral acid (6). Carbon-14 labeled (1) was obtained in two steps using sodium [14C]-cyanide in a modified Strecker reaction followed by amide bond formation with acid (6) in 74% overall radiochemical yield. The phosphate salt of this compound was produced by treatment with phosphoric acid in methanol in 97% yield.

Cite this article as:

Latli Bachir, Hrapchak Matt, C. Lorenz Jon, A. Busacca Carl and Senanayake Chris, Synthesis of a Potent Cathepsin S Inhibitor Labeled with Deuterium and Carbon-14, Current Radiopharmaceuticals 2012; 5 (4) . https://dx.doi.org/10.2174/1874471011205040314