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Synthesis of SCH 42427 labelled with 14 C in two different positions
Author(s) -
Hesk D.,
Bowlen C.,
Duelfer T.,
Koharski D.,
McNamara P.,
Saluja S.
Publication year - 1992
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.2580310604
Subject(s) - chemistry , yield (engineering) , enantiomer , sodium iodide , high performance liquid chromatography , molecule , iodide , chemical synthesis , sodium , radiochemistry , chromatography , stereochemistry , combinatorial chemistry , organic chemistry , in vitro , biochemistry , materials science , metallurgy
Abstract [ 14 C]‐Sch 42427 was synthesized by two different methods, resulting in incorporation of the label in different parts of the molecule. In the first synthesis [benzyl‐α‐ 14 C]‐Sch 42427 was synthesized in overall 1.7% yield via a 6 step procedure, using [ 14 C]‐trimethyl sulphoxonium iodide as the source of label. The second synthesis gave rise to [SO 2 ‐ 14 CH 3 ]‐Sch 42427, which was prepared via a 2 step procedure from [ 14 C]‐sodium thiomethoxide. Radiochemical purities were greater than 99% for both batches, and analysis by chiral hplc failed to detect any of the undesired S,S enantiomer.