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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

✍ Scribed by Douglas D. Dischino; Che-Wah Lee; Makonen Belema; Christopher Zusi

Publisher
John Wiley and Sons
Year
2003
Tongue
French
Weight
97 KB
Volume
46
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Carbon‐14 labeled (R)‐3‐fluoro‐4‐(2′‐(5′′, 6′′, 7′′, 8′′‐tetrahydro‐5′′, 5′′, 8′′, 8′′‐tetramethyl‐2′′‐naphthyl)‐[2′‐hydroxy‐^14^C])[carbonyl‐^14^C]acetamidobenzoic acid, 1, was prepared in a six step radioactive synthesis from diethyl [carboxylate‐^14^C~1,2~] 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.

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