Abstract
Abstract The degradation of cyclophosphamide in neutral or slightly acidic aqueous solution starts with an intramolecular alkylation leading to an intermediary bicyclic compound which hydrolyses immediately and exclusively to a nine-membered heterocycle. Subsequent acid-catalyzed hydrolysis of the P-N-bond leads to a phosphoric acid monoester. In strongly acidic solutions (1 N HC1) cyclophosphamide decomposes exclusively to bis(2-chloroethyl)-amine and to the corresponding phosphoric acid monoester H2N(CH2)3OP(O)(OH)2. In solid samples of cyclophosphamide, heated up to its melting point, the first pathway predominates over the second one. The structures of the phosphorus compounds were established by 1H and 31P NMR spectroscopy, and synthesis. The structure of the bicyclic compound 2 is confirmed by a single crystal X-ray diffraction study which allows an explanation for the selective and immediate hydrolysis with formation of a nine-membered heterocycle and for the absence of the isomer with a six-membered ring.
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