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The synthesis of spiromustine ‐d 8 . A general approach to octadeuterated nitrogen mustards
Author(s) -
Huguenin Philipp N.,
Kelley James A.
Publication year - 1985
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.2580220806
Subject(s) - diethanolamine , chemistry , deuterium , moiety , ethylene glycol , yield (engineering) , nitrogen , hydrogen–deuterium exchange , ethylene , organic chemistry , hydrogen , catalysis , physics , materials science , quantum mechanics , metallurgy
The synthesis of deuterium labelled spiromustine, a potential new antitumor agent designed specifically for neoplasms of the central nervous system, is described. Eight deuterium atoms have been incorporated specifically into the nitrogen mustard moiety to provide a deuterated internal standard suitable for selected ion monitoring by GC/MS. Starting with ethylene glycol‐d 6 , diethanolamine‐d 8 is produced efficiently in good yield with no deuterium exchange via a 2‐imino‐1,3‐oxazolidine intermediate. The resultant diethanolamine‐d 8 may then be used to synthesize spiromustine‐d 8 or other octadeuterated nitrogen mustards.