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Synthesis of the enantiomers of the dual function 2-nitroimidazole radiation sensitizer RB 6145

✍ Scribed by Anthony D. Sercel; Vladimir G. Beylin; Mark E. Marlatt; Boguslawa Leja; H. D. Hollis Showalter; André Michel

Publisher: Journal of Heterocyclic Chemistry
Year: 2006
Tongue: English
Weight: 464 KB
Volume: 43
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570430625

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✦ Synopsis

Abstract

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Short, efficient pathways are described for the synthesis of racemic 2‐nitroimidazole radiation sensitizer RB‐6145 (2a) and each of its corresponding (R)‐ and (S)‐enantiomers (2b and 2c, respectively). The synthesis of each enantiomer commences with the appropriate chiral epichlorohydrin and utilizes a novel application of 3‐trimethylsilyl‐2‐oxazolidinone (3b) as a mild, safe surrogate for highly toxic aziridine. The synthesis of the (R)‐enantiomer (2b) has been successfully scaled up to provide multi‐kilo quantities of material for early stage preclinical evaluation.

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