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Synthesis of 3 H‐labeled 2‐hydroxy‐N‐[(1,3,3‐trimethyl‐[4,5,6‐ 3 H]cyclohexyl)methyl]‐5‐azidobenzamide, a photoaffinity analog of an influenza fusion inhibitor
Author(s) -
Dischino Douglas D.,
Cianci Christopher,
Krystal Mark,
Meanwell Nicholas A.,
Morimoto Hiromi,
Pearce Bradley C.,
Williams Philip,
Yu KuoLong
Publication year - 1999
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199910)42:10<965::aid-jlcr255>3.0.co;2-k
Subject(s) - chemistry , photoaffinity labeling , high performance liquid chromatography , amine gas treating , chemical synthesis , tritium , chloride , stereochemistry , chromatography , organic chemistry , receptor , biochemistry , in vitro , physics , nuclear physics
Synthesis of 3 H‐labeled 2‐hydroxy‐N‐[(1,3,3‐trimethyl‐[4,5,6‐ 3 H]cyclohexyl)methyl]‐5‐azidobenzamide, a photoaffinity analog of an influenza fusion inhibitor, is reported. Tritiation of a mixture of N‐(t‐butoxycarbonyl)‐1,3,3‐trimethylcyclohex‐4 (or 5)‐enylmethylamine via T 2 and Pd/C, followed by coupling of the deprotected tritiated amine with acetyl 5‐azidosalicylic acid chloride yielded the penultimate product. Subsequent deprotection and normal phase HPLC purification yielded the target compound with a radiochemical purity >99% and a specific activity of 63 Ci/mmol. Copyright © 1999 John Wiley & Sons, Ltd.