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Synthesis of tritium‐labeled azaline B acetate
Author(s) -
Walker Donald G.,
Hoerr David C.,
Leister William H.,
Weaner Larry E.
Publication year - 1997
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(199702)39:2<147::aid-jlcr953>3.0.co;2-3
Subject(s) - chemistry , trifluoroacetic acid , tritium , anhydrous , methylene , acetic acid , homonuclear molecule , nuclear magnetic resonance spectroscopy , chloride , radiochemistry , nuclear chemistry , chromatography , organic chemistry , physics , molecule , nuclear physics
Reaction of azaline B acetate ( 1 ) with freshly prepared trifluoroacetyl hypoiodite in trifluoroacetic acid ‐ methylene chloride solution under anhydrous conditions produced a complex mixture of products from which compounds 2 and 3 , resulting from iodination at the 1′‐and 8′‐positions of the Ac‐D Nal 1 residue, were isolated by preparative reversed‐phase HPLC chromatography. Mass spectral analysis and 1 H, 2D DQF‐COSY and homonuclear 2D J‐resolved NMR experiments confirmed these structures. Reductive tritiation of 2 over 10% Pd/C in EtOH ‐ DMF (1:9, v/v) with 50 Ci T 2 followed by chromatographic purification and salt exchange gave 37.5 mCi of tritiated azaline B acetate ( 4 ) having >98% chemical and radiochemical purities and a specific radioactivity of 11.2 Ci / mmol. A single peak at 7.59 ppm was observed in the proton decoupled tritium NMR spectrum. © 1997 John Wiley & Sons, Ltd.