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Synthesis of 17O (and 18O) labelled isophosphoramide mustard

✍ Scribed by Sung Y. Han; Ellen M. Shulman-Roskes; Konrad Misiura; Lawrence W. Anderson; Edward Szymajda; Michael P. Gamcsik; Young H. Chang; Susan M. Ludeman

Publisher
John Wiley and Sons
Year
1994
Tongue
French
Weight
334 KB
Volume
34
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The ifosfamide metabolite isophosphoramide mustard (IPM) was synthesized with isotopic enrichment at oxygen. Labelled benzaldehyde was made by exchange with isotopically enriched water (13.4 atom % ^17^0, 25.5 atom % ^18^0) and this was then reduced with sodium borohydride to give labelled benzyl alcohol (72% yield). Triethylamine and labelled benzyl alcohol were added to POCl~3~/CHCl~3~ at −23°C. Subsequent addition of 2‐chloroethylamine hydrochloride (2 equiv) and then triethylamine (4.4 equiv) (−15°C) provided ^17^0/^18^0 enriched N,N′‐bs‐(2‐chloroethyl)phosphorodiamidic acid phenylmethyl ester [61%, BzOP(O)(NHCH~2~CH~2~Cl)~2~]. Catalytic (10% Pd/C) hydrogenation of this ester at atmospheric pressure gave IPM (22%). GC/MS was used to determine mole percent enrichments of 9.3% ^17^0 and 17.9% ^18^0 for IPM (single labelling within one molecule).

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