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Synthesis of deuterium-, tritium-, and carbon-14-labeled BILN2061, a potent hepatitis C virus protease inhibitor

✍ Scribed by Bachir Latli; Matt Hrapchak; Vida Gorys; Carl A. Busacca; Chris Senanayake

Publisher
John Wiley and Sons
Year
2005
Tongue
French
Weight
118 KB
Volume
48
Category
Article
ISSN
0022-2135

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✦ Synopsis

Hepatitis C virus (HCV) serine protease is a target for antiviral therapy against HCV infection, a leading cause of liver transplantation in the US. BILN2061, (1S, 4R, 6S, 7Z, 14S, 18R)-14-cyclopentyloxycarbonylamino-18-[2-(2-isopropylamino-thiazol-4-yl)-7-methoxyquinolin-4-yloxy]-2,15-dioxo-3,16-diazatricyclo[14.3.0.0 4,6 ]nonadec-7ene-4-carboxylic acid, is a potent inhibitor of HCV and the first compound in this class of cyclic peptides in human trials. Here, we report the synthesis of deuteriumlabeled BILN2061 with isotopic enrichment of 99%, tritium-labeled BILN2061 with a specific activity of 17.1 GBq/mmol, and carbon-14-labeled BILN2061 with a specific activity of 1.83 GBq/mmol. The isotopes were incorporated via a Hantzsch thiazole synthesis of labeled isopropyl thiourea and a-bromoketone intermediate. The preparation of labeled isopropyl thiourea is reported.

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