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Radiolabelling of NNC 05‐1869, a compound for treatment of diabetic neuropathy
Author(s) -
Valsborg Jacob S.,
Foged Christian
Publication year - 2002
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.530
Subject(s) - chemistry , yield (engineering) , electrophile , labelling , high performance liquid chromatography , tin , tritium , catalysis , chromatography , carbon fibers , specific activity , organic chemistry , medicinal chemistry , biochemistry , enzyme , materials science , physics , composite number , nuclear physics , metallurgy , composite material
Synthesis of 3 H‐, 14 C‐ and 125 I‐labelled NNC 05‐1869 is described. The 3 H‐label was obtained by catalytic hydrogenation of a carbon–carbon double bond with tritium gas, which after purification yielded 470 µCi [ 3 H]NNC 05‐1869 with a specific radioactivity of 36 Ci/mmol. 14 C‐labelling was accomplished in three steps, including a chiral HPLC separation, starting from ethyl 3‐[carboxyl‐ 14 C]piperidinecarboxylate ( 1 ). The overall radiochemical yield was 1.5 mCi of [carboxyl‐ 14 C]NNC 05‐1869 (14%) with a specific radioactivity of 55 mCi/mmol. Electrophilic aromatic iododestannylation of the tin‐precursor NNC 47‐4310 with Na 125 I resulted in a cis/trans mixture, which was separated on RP‐HPLC to give the two isomers in 20% and 22%, yield, respectively. Copyright © 2002 John Wiley & Sons, Ltd.
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