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Synthesis of deuterium‐labelled chlorhexidine
Author(s) -
Moser M.,
Hudlicky T.,
Sadeghi S.,
Sternin E.
Publication year - 2007
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.1383
Subject(s) - chemistry , yield (engineering) , hydrochloride , chlorhexidine , chemical synthesis , diol , hydrolysis , deuterium , labelling , organic chemistry , medicine , biochemistry , materials science , physics , dentistry , quantum mechanics , metallurgy , in vitro
The synthesis of deuterated chlorhexidine hydrochloride is reported. The specific labelling of the saturated chain is achieved through the combination of the previously reported synthesis of 2,2,3,3,4,4,5,5‐( 2 H 8 )‐hexane‐1,6‐diol and a synthesis of carbon‐14 labelled chlorhexidine. This synthesis begins with commercially available hex‐2,4‐yne‐1,6‐diol, its protection as a bis‐tetrahydropyranylether, and exhaustive deuterogenation under rhodium catalysis to produce, after acid hydrolysis of the protecting groups, the saturated octadeuterated 1,6‐hexanediol. Conversion of this material in two steps to the corresponding 1,6‐diaminohexane was followed by the generation of guanidines with dicyanimide and final condensation with p ‐chloroaniline. The title compound was obtained in 10 chemical steps and in 6% overall yield. Copyright © 2007 John Wiley & Sons, Ltd.