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Boc-protected 1-(3-oxocycloalkyl)ureas via a one-step Curtius rearrangement: mechanism and scope |
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| Authors: | Xianyu Sun Rachita Rai Jeffrey R. Deschamps Alexander D. MacKerell Jr. Alan I. Faden Fengtian Xue |
| Affiliation: | 1. Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Baltimore, MD 21201, United States;2. Department of Anesthesiology, University of Maryland School of Medicine, 20 Penn Street, Baltimore, MD 21201, United States;3. Naval Research Laboratory, Code 6930, 4555 Overlook Ave., Washington, DC 20375, United States;4. College of Animal Science and Technique, Heilongjiang Bayi Agriculture University, Daqing 163319, Heilongjiang, PR China |
| Abstract: | 1-(3-Oxocyclobutyl) carboxylic acid (4a) was converted into N-Boc-protected 1-(3-oxocyclobutyl) urea (5a), a key intermediate for the preparation of agonists of metabotropic glutamate receptor 5, in one-step when treated with diphenyl phosphoryl azide and triethylamine in tert-butanol. The mechanism of the reaction involves a nucleophilic addition of the in situ generated tert-butyl carbamate to the isocyanate intermediate. This reaction is applicable to other 1-(3-oxocycloalkyl) carboxylic acids but not to linear γ-keto carboxylic acids. |
| Keywords: | 1-(3-Oxo)ureas Curtius rearrangement Carbamoylcarbamate γ-Keto carboxylic acid 1-(3-Oxocyclobutyl) carboxylic acid |
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