SYNTHESIS OF N-15 LABELED ISOPHOSPHORAMIDE MUSTARD

Authors
SHULMANROSKES EM GAMCSIK MP COLVIN OM CHANG YH KOO KI LUDEMAN SM
Citation
Em. Shulmanroskes et al., SYNTHESIS OF N-15 LABELED ISOPHOSPHORAMIDE MUSTARD, Journal of labelled compounds & radiopharmaceuticals, 34(3), 1994, pp. 231-237
Citations number
13
Categorie Soggetti
Chemistry Analytical","Pharmacology & Pharmacy
Journal title
Journal of labelled compounds & radiopharmaceuticals → ACNP
ISSN journal
03624803
Volume
34
Issue
3
Year of publication
1994
Pages
231 - 237
Database
ISI
SICI code
0362-4803(1994)34:3<231:SONLIM>2.0.ZU;2-7
Abstract
The ifosfamide metabolite isophosphoramide mustard (IPM) was synthesiz ed with isotopic enrichment at each nitrogen site. Glycine-N-15 was co nverted to 2-chloroethylamine-N-15 hydrochloride (4 steps, 21% net yie ld) which was then reacted with phenyl dichlorophosphate to provide N, N'-bis(2-chloroethyl)phosphorodiamidic-N-15(2) acid phenyl ester [62%, PhOP(O) ((NHCH2CH2Cl)2)-N-15]. Catalytic hydrogenation of this phenyl ester followed by the addition of cyclohexylamine (CHA) provided IPM- N-15(2) as the CHA salt (63%).