Premium
Synthesis of carbon‐13 labeled ibuprofen
Author(s) -
Hsi R. S. P.,
Stelzer L. S.,
Stolle W. T.
Publication year - 1989
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.2580271003
Subject(s) - chemistry , isopropyl , wittig reaction , acetone , ibuprofen , side chain , propenyl , carbon fibers , reinforced carbon–carbon , carbon 13 nmr , organic chemistry , carbon 13 , carbon chain , medicine , materials science , composite material , composite number , pharmacology , polymer , physics , quantum mechanics
This report describes the synthesis of ibuprofen of labeled with carbon‐13 either at the terminal methyl carbons, or at the methine carbon of the isobutyl side chain. The synthetic route involves the removal of the isopropyl group in the isobut I side‐chain of ibuprofen via 2‐[4‐(2‐methyl‐1‐propenyl)phenyl] propionic acid followed by restoration of the isopropyl group with a Wittig reaction, using appropriate carbon‐1 3 labeled acetone as the precursor of the isopropyl group. Interesting NMR coupling data attributable to phosphorous and carbon‐13 are presented in the experimental section.