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Synthesis of carbon‐14 labeled LTD 4 antagonist MK‐571
Author(s) -
Dean Dennis C.,
Melillo David G.,
Ellsworth Robert L.
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.2580290211
Subject(s) - chemistry , aldehyde , hemiacetal , nitrile , trimethylsilyl cyanide , yield (engineering) , sodium cyanide , hydrolysis , cyanohydrin , antagonist , condensation reaction , trimethylsilyl , stereochemistry , cyanide , medicinal chemistry , organic chemistry , biochemistry , materials science , receptor , metallurgy , catalysis
The synthesis of (E)‐5‐(3‐(2‐(7‐chloroquinolin‐2‐yl)ethenyl)‐ phenyl)‐[5‐ 14 C]‐4,6‐dithianonane dicarboxylic acid N, N‐dimethylamide ([ 14 C]MK‐571), a high‐affinity LTD 4 antagonist, from sodium [ 14 C]cyanide via a five step sequence is described. Condensation of 3‐[ 14 C]cyanobenzaldehyde with 7‐chloroquinaldine followed by nitrile reduction provided the [ 14 C]aldehyde 2. The pivotal formation of the penultimate unsymmetrical dithioacetal intermediate was accomplished in a selective manner from aldehyde 2 by way of an O‐trimethylsilyl hemiacetal intermediate. Subsequent ester hydrolysis afforded [ 14 C]MK‐571 in 14% overall radiochemical yield.