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Synthesis of four isotopically labeled forms of a proteasome inhibitor, bortezomib

✍ Scribed by Yuexian Li; Mihaela Plesescu; Patrick Sheehan; J. Scott Daniels; Shimoga R. Prakash

Publisher
John Wiley and Sons
Year
2007
Tongue
French
Weight
117 KB
Volume
50
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

D~2~‐3‐methyl‐1‐[[(2S)‐1‐oxo‐3‐phenyl‐2‐[(pyrazinylcarbonyl)amino]propyl]‐amino]butyl] boronic acid ([D~2~]bortezomib), a proteasome inhibitor, was synthesized in 11 steps from __iso__butyryl chloride. Key steps in the synthesis included formation of the __iso__butyryl boronic acid via Grignard reaction and preparation of the chiral chloride using Matteson reaction. [^13^C~9~]bortezomib, [D~5~]bortezomib, and [D~1~]bortezomib were similarly synthesized from appropriate labeled precursors. Copyright © 2007 John Wiley & Sons, Ltd.

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