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Synthesis and NMR‐analysis of deuterated and tritiated cyclooctyl acetic acid
Author(s) -
Kaspersen Frans M.,
Schlachter Irene H. G.,
Funke Carel W.,
Wagenaars Gerard N.,
Mellema JanRemt
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.2580290514
Subject(s) - chemistry , acetic acid , cyanoacetic acid , hydrolysis , carbon 13 nmr , deuterium , cyanide , proton nmr , tritiated water , organic chemistry , tritium , nuclear chemistry , physics , quantum mechanics , nuclear physics
Abstract To increase the bio‐availability of naturally occurring steroids, esterification of the 17‐hydroxy position is a useful approach. Besides (branched) alkanecarboxylic acids 1 ) and cyclohexanecarboxylic acid 2 ) also cyclooctyl acetic acid ( 1 ) was applied. To establish the biological fate of the cyclooctyl acetic acid part of steroids the tritiated molecule was synthesized (Figure 1). Cyclooctanone ( 3 ) was condensed with cyanoacetic acid 3 ) and the resulting cyanide ( 4 ) was hydrolyzed to cyclooctenyl acetic acid ( 2a ) 4 ) which contained according to 1 H NMR and 13 C NMR 20% of the isomeric 2b ( 1 H NMR (C 2 HCl 3 ): 5,58 ppm (t, CH of 2a ) and 5,63 ppm (br.s CH of 2b ) 13 C NMR(C 2 HCl 3 ): 129,6 ppm (CH of 2a ) and 115,0 ppm (CH of 2b )).