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Synthesis of [ 3 H 2 ]‐( R , R )‐1,2‐diaminocyclohexaneoxalatoplatinum(II), [ 3 H 2 ]‐Oxaliplatin
Author(s) -
Burgos Alain,
Ellames George J.
Publication year - 1998
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/(sici)1099-1344(199805)41:5<443::aid-jlcr100>3.0.co;2-w
Subject(s) - chemistry , yield (engineering) , hydrolysis , oxaliplatin , ene reaction , cyclohexene , cyclohexane , tartaric acid , medicinal chemistry , diamine , tritium , catalysis , organic chemistry , medicine , materials science , colorectal cancer , cancer , metallurgy , citric acid , physics , nuclear physics
A synthesis of [ 3 H 2 ]‐( R , R )‐1,2‐diaminocyclohexaneoxalatoplatinum(II), [ 3 H 2 ]‐Oxaliplatin, 2 , is described. rac‐trans ‐4‐Cyclohexene‐1,2‐dicarboxylic acid diethyl ester, 6 , was converted to rac‐trans ‐1,2‐diaminocyclohex‐4‐ene, 7 , by modification of known chemistry aimed at avoiding reported hazards. Resolution of the diamine, 7 , with L‐(+)‐tartaric acid afforded the ( R , R )‐1,2‐diaminocyclohex‐4‐ene, 8 , which was converted to the ( R , R )‐1,2‐bis( tert ‐butoxy‐carbamino)cyclohex‐4‐ene, 10 , and tritiated to yield [ 3 H 2 ]‐( R , R )‐1,2‐bis( tert ‐butoxycarbamino)‐cyclohexane, 11 . Hydrolysis of 11 afforded [ 3 H 2 ]‐( R , R )‐1,2‐diaminocyclohexane, 12 , which was converted to the desired [ 3 H 2 ]‐( R , R )‐1,2‐diaminocyclohexaneoxalatoplatinum(II), [ 3 H 2 ]‐Oxaliplatin, 2 . © 1998 John Wiley & Sons, Ltd.
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