Synthesis of carbon-14 labeled (R)-3-fluoro-4-(2′-(5′′, 6′′, 7′′, 8′′-tetrahydro-5′′, 5′′, 8′′, 8′′-tetramethyl-2′′-naphthyl)-[2′-hydroxy-14C])[carbonyl-14C]acetamidobenzoic acid

• Published in: Journal of labelled compounds & radiopharmaceuticals Vol. 46; no. 2; pp. 159 - 165
• Main Authors: Dischino, Douglas D., Lee, Che-Wah, Belema, Makonen, Zusi, Christopher
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.02.2003; Wiley
• Subjects: 2]oxalate; Biochemical Research Methods; Biochemistry & Molecular Biology; carbon-14; Chemistry; Chemistry, Analytical; Chemistry, Medicinal; Condensed benzenic and aromatic compounds; diethyl [carboxyl-14C1; diethyl [carboxyl‐14C1,2]oxalate; Exact sciences and technology; Life Sciences & Biomedicine; Organic chemistry; Pharmacology & Pharmacy; Physical Sciences; Preparations and properties; retinoid; Science & Technology; GAMMA; carbon-14; diethyl [carboxyl-C-14(1,2)]oxalate; retinoid; Radiolabelling; Carboxylic acid; Hydroxyamide; Retinoid; Benzenic compound; Fluorine Organic compounds; R configuration; Chemical synthesis; Carbon 14; Naphthalene derivatives
• DOI: 10.1002/jlcr.654
• ISSN: 0362-4803

Carbon‐14 labeled (R)‐3‐fluoro‐4‐(2′‐(5′′, 6′′, 7′′, 8′′‐tetrahydro‐5′′, 5′′, 8′′, 8′′‐tetramethyl‐2′′‐naphthyl)‐[2′‐hydroxy‐14C])[carbonyl‐14C]acetamidobenzoic acid, 1, was prepared in a six step radioactive synthesis from diethyl [carboxylate‐14C1,2] oxalate. The penultimate compound was purified by chiral HPLC, which following deprotection yielded 1 in an overall radiochemical yield of 6.8%. The specific activity of the final product was found to be 24.5 µCi/mg with a radiochemical purity of > 99% as determined by HPLC. Derivatization of 1 via trimethylsilyl diazomethane to the corresponding methyl ester 9, followed by chiral HPLC analysis, demonstrated that 1 had an optical purity of > 99% ee. Copyright © 2002 John Wiley & Sons, Ltd.