Synthesis of 3-hydroxycyclophosphamide and studies related to its possible role in the metabolism of cyclophosphamide

JA Brandt, SM Ludeman, G Zon, W Egan…

Index: Brandt, Joan A.; Ludeman, Susan Marie; Zon, Gerald; Todhunter, John A.; Egan, William; Dickerson, Ruth Journal of Medicinal Chemistry, 1981 , vol. 24, # 12 p. 1404 - 1408

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Citation Number: 9

Abstract

Hydrogenolysis of 3-(benzyloxy) cyclophosphamide (10) using Pd/C catalyst and ethyl acetate as solvent leads to the formation of 3-hydroxycyclophosphamide (3,-20%) and cyclophosphamide (1,-10%), accompanied by regioselective hydrogen-exchange reactions at the C-4 and C-5 positions in 3 and 1. A variety of oxidizing reagents and liver microsomal incubation failed to provide evidence NMR) for conversion of 1 into 3, whereas identical ...