Direct Carbon Isotope Exchange through Decarboxylative Carboxylation.

Autor: Kingston C; Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States., Wallace MA; Radiochemistry , Bristol-Myers Squibb Company , P.O. Box 4000, Princeton , New Jersey 08543 , United States., Allentoff AJ; Radiochemistry , Bristol-Myers Squibb Company , P.O. Box 4000, Princeton , New Jersey 08543 , United States., deGruyter JN; Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States., Chen JS; Automated Synthesis Facility , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States., Gong SX; Radiochemistry , Bristol-Myers Squibb Company , P.O. Box 4000, Princeton , New Jersey 08543 , United States., Bonacorsi S Jr; Radiochemistry , Bristol-Myers Squibb Company , P.O. Box 4000, Princeton , New Jersey 08543 , United States., Baran PS; Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2019 Jan 16; Vol. 141 (2), pp. 774-779. Date of Electronic Publication: 2019 Jan 03.
DOI: 10.1021/jacs.8b12035
Abstrakt: A two-step degradation-reconstruction approach to the carbon-14 radiolabeling of alkyl carboxylic acids is presented. Simple activation via redox-active ester formation was followed by nickel-mediated decarboxylative carboxylation to afford a range of complex compounds with ample isotopic incorporations for drug metabolism and pharmacokinetic studies. The practicality and operational simplicity of the protocol were demonstrated by its use in an industrial carbon-14 radiolabeling setting.
Databáze: MEDLINE
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