1. Synthesis of [14C]-radiolabelled entecavir
- Author
-
Kucera David J, Marc Ogan, J. Kent Rinehart, and Yadagiri Pendri
- Subjects
Chemistry ,Organic Chemistry ,Epoxide ,Entecavir ,Biochemistry ,Chemical synthesis ,High-performance liquid chromatography ,Medicinal chemistry ,Analytical Chemistry ,chemistry.chemical_compound ,Yield (chemistry) ,Drug Discovery ,medicine ,Organic chemistry ,Purine derivative ,Radiology, Nuclear Medicine and imaging ,Orthoester ,Spectroscopy ,medicine.drug - Abstract
Radiolabelled [14C]entecavir, (1), was prepared in 12 steps from (1S,2R,3S,5R)-3-(benzyloxy)-2-(benzyloxymethyl)-6-oxa-bicyclo[3.1.0]hexane 2. The chemical yield of [14C]entecavir was 14% from the epoxide 2. Introduction of [14C] radiolabel was achieved by elaboration of 4,5-diaminopyrimidine 8 with triethyl[14C]orthoformate to purine derivative 9. The radiochemical yield of [14C]entecavir from triethyl[14C]orthoformate was 11.3%. Radiochemical purity of [14C]entecavir determined by HPLC was 99.8%. The specific activity of [14C]entecavir was 108 µCi/mg (29.9 mCi/mmol). Copyright © 2005 John Wiley & Sons, Ltd.
- Published
- 2005
- Full Text
- View/download PDF