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

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...

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Veröffentlicht in:Journal of labelled compounds & radiopharmaceuticals 2003-02, Vol.46 (2), p.159-165
Hauptverfasser: Dischino, Douglas D., Lee, Che-Wah, Belema, Makonen, Zusi, Christopher
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0362-4803
1099-1344
DOI:10.1002/jlcr.654