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Synthesis of [ 14 C]ciladopa
Author(s) -
Hicks D. R.,
Dolak L.,
Foss D.
Publication year - 1988
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.2580251203
Subject(s) - chemistry , hydrochloride , ketone , yield (engineering) , alcohol , barium carbonate , chloride , nuclear chemistry , salt (chemistry) , carbonate , enantiomer , medicinal chemistry , carbon 14 , barium chloride , barium , radiochemistry , organic chemistry , raw material , materials science , physics , quantum mechanics , metallurgy
[ 14 C]Ciladopa (S(−)‐2‐[4‐[[2‐ 14 C]‐2‐hydroxy‐2‐(3,4‐dimethoxyphenyl)ethyl]‐1‐piperazinyl]‐2,4,6‐cycloheptatrien‐1‐ one hydrochloride; AY‐27,110 hydrochloride) has been synthesized in six steps incorporating [ 14 C]carbon dioxide. [7‐ 14 C]Acetoveratrole, obtained from veratric acid via the acid chloride, was brominated and coupled with a troponylpiperazine salt. The resulting ketone was stereospecifically reduced microbiologically to give the S(−) enantiomer of the corresponding alcohol. Two batches of [ 14 C]ciladopa were produced, giving a combined overall yield of 25% from [ 14 C]barium carbonate (sp. act. 44.7 ± 0.6 and 43.4 ± 0.8 μCi/mg; 99.2 and 98.9 % radiochemical purity, respectively).