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Synthesis of 15N labelled isophosphoramide mustard

✍ Scribed by Ellen M. Shulman-Roskes; Michael P. Gamcsik; O. Michael Colvin; Young H. Chang; Kyo I. Koo; Susan M. Ludeman

Publisher: John Wiley and Sons
Year: 1994
Tongue: French
Weight: 293 KB
Volume: 34
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580340305

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✦ Synopsis

Abstract

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%).

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