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Synthesis of four isotopically labeled forms of a proteasome inhibitor, bortezomib
Author(s) -
Li Yuexian,
Plesescu Mihaela,
Sheehan Patrick,
Scott Daniels J.,
Prakash Shimoga R.
Publication year - 2007
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.1173
Subject(s) - chemistry , bortezomib , proteasome inhibitor , boronic acid , chloride , proteasome , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , multiple myeloma , medicine
[D 2 ](1 R )‐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.