A concise synthesis of a β-lactamase inhibitor.

Department of Process Research, Merck and Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA.
Organic Letters (Impact Factor: 6.14). 09/2011; 13(20):5480-3. DOI: 10.1021/ol202195n
Source: PubMed

ABSTRACT MK-7655 (1) is a β-lactamase inhibitor in clinical trials as a combination therapy for the treatment of bacterial infection resistant to β-lactam antibiotics. Its unusual structural challenges have inspired a rapid synthesis featuring an iridium-catalyzed N-H insertion and a series of late stage transformations designed around the reactivity of the labile bicyclo[3.2.1]urea at the core of the target.

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