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Synthesis of [5‐ 14 C]‐1,1,12,12‐tetraethoxy‐4,9‐diazadodecane dinitrate
Author(s) -
Somayaji Vijayalakshmi V.,
Hall Tse W.,
Wiebe Leonard I.,
Knaus Edward E.,
Demers James P.
Publication year - 1989
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.2580270412
Subject(s) - chemistry , yield (engineering) , nitric acid , nuclear chemistry , succinimide , radiochemistry , chloride , specific activity , aluminum hydride , succinic acid , lithium (medication) , chemical synthesis , organic chemistry , medicinal chemistry , catalysis , biochemistry , enzyme , medicine , materials science , metallurgy , endocrinology , methoxide , in vitro
The reaction of [1‐ 14 C]succinyl chloride with 3,3‐diethoxypropylamine ( 4 ) afforded N,N'‐bis(3,3‐diethoxypropyl[(1‐ 14 C]succinic acid diamide ( 6 , 43.9% chemical and radiochemical yield) and N‐(3,3‐diethoxypropyl[1‐ 14 C]succinimide ( 7 , 35.8% chemical and 35.5% radiochemical yield). Reduction of 6 using lithium aluminum hydride followed by reaction with concentrated nitric acid yielded [5‐ 14 C]‐1,1,12,12‐tetraethoxy‐4 9‐diazadodecane dinitrate ( 8 ) in 16% overall radiochemical yield from [1‐ 14 C]succinyl chloride with a specific activity of 55.4 mCi/mmol (2.05 GBq/mmol) and a radiochemical purity of 97.3%.