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Development of a Safe and Efficient Two-Step Synthesis for Preparing 1-Bromoacetyl-3,3-dinitroazetidine, a Novel Clinical Anticancer Candidate

2012; American Chemical Society; Volume: 16; Issue: 3 Linguagem: Inglês

10.1021/op2003216

1520-586X

Nicholas A. Straessler, Michael W. Lesley, Louis F. Cannizzo,

Receptor Mechanisms and Signaling

An efficient process for synthesizing and isolating a new investigative anticancer agent, 1-bromoacetyl-3,3-dinitroazetidine, is described. The reaction entails a sequence of oxidative nitration followed by acylative dealkylation. The methods reported give 50–60-g batches of high-purity product without a designated purification step. The reaction conditions have been designed to mitigate the safety concerns associated with gem-dinitroazetidines. Some observations on the acylative dealkylation mechanism are discussed.