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Synthesis of 15 N labelled isophosphoramide mustard
Author(s) -
ShulmanRoskes Ellen M.,
Gamcsik Michael P.,
Colvin O. Michael,
Chang Young H.,
Koo Kyo I.,
Ludeman Susan M.
Publication year - 1994
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.2580340305
Subject(s) - chemistry , cyclohexylamine , yield (engineering) , hydrochloride , glycine , metabolite , catalysis , medicinal chemistry , catalytic hydrogenation , salt (chemistry) , nitrogen , nitrogen mustard , organic chemistry , amino acid , biochemistry , medicine , materials science , surgery , chemotherapy , cyclophosphamide , metallurgy
The ifosfamide metabolite isophosphoramide mustard (IPM) was synthesized with isotopic enrichment at each nitrogen site. Glycine‐ 15 N was converted to 2‐chloroethylamine‐ 15 N hydrochloride (4 steps, 21% net yield) which was then reacted with phenyl dichlorophosphate to provide N,N ′‐bis(2‐chloroethyl)phosphorodiamidic‐ 15 N 2 acid phenyl ester [62%, PhOP( O ) ( 15 NHCH 2 CH 2 Cl) 2 ]. Catalytic hydrogenation of this phenyl ester followed by the addition of cyclohexylamine (CHA) provided IPM‐ 15 N 2 as the CHA salt (63%).