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Synthesis of 14 C‐labeled and tritiated AMPA potentiator LY450108
Author(s) -
Czeskis Boris A.,
O'Ban Douglas D.,
Wheeler William J.,
Clodfelter Dean K.
Publication year - 2005
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.899
Subject(s) - chemistry , potentiator , acylation , nitro , amine gas treating , derivative (finance) , chloride , alcohol , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , alkyl , economics , financial economics , immunology , biology
Asymmetric synthesis of AMPA potentiator LY450108‐[ 14 C] containing 14 C‐label attached to the chiral center of the molecule, was accomplished based on Evans' chiral oxazolidinone auxiliary method. Diastereoselective methylation of p ‐nitrophenylacetic acid derivative was used as a key step. The auxiliary was reductively removed, and the resulting primary alcohol was converted into the corresponding amine. Its sulfonylation, reduction of the aromatic nitro group, and acylation with 3,5‐difluorobenzoyl chloride led to the final product. The synthesis of tritiated LY450108 is also detailed. Copyright © 2005 John Wiley & Sons, Ltd.