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Synthesis of [ 14 C]A‐62514, a radiolabelled derivative of erythromycin a, via [2‐ 14 C]N, N‐dimethylethylenediamine
Author(s) -
Surber Bruce W.,
Baker William R.,
Seif Louis
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.2580290105
Subject(s) - chemistry , yield (engineering) , ammonium hydroxide , methanol , medicinal chemistry , derivative (finance) , erythromycin , salt (chemistry) , ammonium , chemical synthesis , nuclear chemistry , hydroxide , stereochemistry , organic chemistry , antibiotics , in vitro , biochemistry , materials science , economics , financial economics , metallurgy
The synthesis of [ 14 C]A‐62514, 11‐deoxy‐11‐[carboxy(2‐dimethylamino‐[1‐ 14 C]ethyl)amino]‐6‐0‐methyl‐erythromycin A 11,12‐(cyclic ester), was performed in five steps. The key intermediate, [2‐ 14 C]N, N‐dimethylethyl‐enediamine, was obtained in 80% yield by reacting Eschenmoser's salt with K 14 CN and reducing the resulting [1‐ 14 C]N, N‐dimethylglycinonitrile with H 12 and Raney Ni in methanol and ammonium hydroxide. The final product was obtained 97% radiochemically pure in an overall radiochemical yield of 14%, with a specific activity of 39 mCi/mmol.