Abstract
AbstractThe 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 % 170, 25.5 atom % 180) and this was then reduced with sodium borohydride to give labelled benzyl alcohol (72% yield). Triethylamine and labelled benzyl alcohol were added to POCl3/CHCl3 at −23°C. Subsequent addition of 2‐chloroethylamine hydrochloride (2 equiv) and then triethylamine (4.4 equiv) (−15°C) provided 170/180 enriched N,N′‐bs‐(2‐chloroethyl)phosphorodiamidic acid phenylmethyl ester [61%, BzOP(O)(NHCH2CH2Cl)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% 170 and 17.9% 180 for IPM (single labelling within one molecule).
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