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Radiosynthesis of [ 11 C]docetaxel
Author(s) -
van Tilburg E. W.,
Franssen E. J. F.,
van der Hoeven J. J. M.,
van der Meij M.,
Elshove D.,
Lammertsma A. A.,
Windhorst A. D.
Publication year - 2004
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.861
Subject(s) - docetaxel , chemistry , radiosynthesis , moiety , yield (engineering) , radiochemistry , positron emission tomography , stereochemistry , nuclear medicine , cancer , medicine , materials science , metallurgy
Docetaxel (Taxotere®) is an accepted chemotherapeutic agent for the treatment of breast cancer and non‐small cell lung cancers. A potential means of predicting response is measuring tumor uptake of [ 11 C]docetaxel using Positron Emission Tomography (PET). The synthetic approach to introduce the 11 C isotope in the 2‐benzoyl moiety of docetaxel unfortunately was unsuccessful. The radiosynthesis of [ 11 C]docetaxel ( 6b , Scheme 1), with the 11 C isotope in the BOC moiety, was however, successful using a second synthetic approach. It started with the reaction of [ 11 C] tert ‐butanol with 1,2,2,2‐tetrachloroethyl chloroformate to give [ 11 C] tert ‐butyl‐l,2,2,2‐tetrachloroethyl carbonate in a good overall yield (62±9%). In the final step, the [ 11 C] tert ‐butoxycarbonylation of the free amine of docetaxel gave [ 11 C]docetaxel 6b in a satisfactory decay corrected yield of 10±1% (from [ 11 C]CO 2 ). Copyright © 2004 John Wiley & Sons, Ltd.