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Synthesis of novel tritium labeled oxamyristic acids
Author(s) -
Devadas Balekudru,
Adams Steven P.,
Gordon Jeffrey I.
Publication year - 1991
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/jlcr.2580290206
Subject(s) - chemistry , alkylation , yield (engineering) , ether , tritium , lithium (medication) , salt (chemistry) , organic chemistry , medicinal chemistry , catalysis , medicine , materials science , physics , nuclear physics , metallurgy , endocrinology
Syntheses of [ 3 H]‐labeled 13‐oxa ( 5 ) and 6‐oxa ( 9 ) myristic acids with specific activity of 137 Ci/mmol and 105 Ci/mmol respectively, starting from the corresponding acetylenic precursors, 12‐methoxy‐10‐dodecynoic acid ( 4 ) and 5‐(3‐octynyloxy)pentanoic acid ( 8 ) are described. The precursor 4 is readily obtained in high yield by alkylation of the lithium salt of methyl propargyl ether with 9‐iodononanoic acid, whereas 8 is obtained by alkylation of 3‐octyn‐1‐ol with t ‐butyl‐5‐bromovalerate under phase transfer conditions, followed by acid catalysed removal of the t ‐butyl group.