title: A modern approach to the synthesis of 2-(4-chlorophenyl)[2-(14)C]thiazol-4-ylacetic acid ([(14)C] fenclozic acid) and its acyl glucuronide metabolite.
abstract: An updated approach to the 1960s synthesis of [(14)C] fenclozic acid from labelled potassium cyanide is presented. By employing modern synthetic methodology and purification techniques, many of the inherent hazards in the original synthesis are avoided or significantly reduced. The concomitant labelled stereoselective synthesis of the key acyl glucuronide metabolite (the 1-β-O-acyl glucuronide) is also described.
authors.affiliation: DMPK IM, AstraZeneca UK Ltd, Mereside, Alderley Park, Macclesfield, Cheshire, SK10 4TG, UK.
authors.forename: David A
authors.initials: DA
authors.lastname: Killick
authors.forename: Nick
authors.initials: N
authors.lastname: Bushby
mesh_terms: D002250:Carbon Radioisotopes / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic / Q000379:methods; D020719:Glucuronides / Q000138:chemical synthesis / Q000737:chemistry; D007553:Isotope Labeling / Q000379:methods; D011190:Potassium Cyanide / Q000737:chemistry; D019275:Radiopharmaceuticals / Q000138:chemical synthesis*; D013844:Thiazoles / Q000138:chemical synthesis*
chemical_list: D002250:Carbon Radioisotopes; D020719:Glucuronides; D019275:Radiopharmaceuticals; D013844:Thiazoles; C100273:fenclozic acid; D011190:Potassium Cyanide
keywords: acyl glucuronide; cyanide; fenclozic acid