1552322-83-4Relevant academic research and scientific papers
Boc-protected 1-(3-oxocycloalkyl)ureas via a one-step Curtius rearrangement: Mechanism and scope
Sun, Xianyu,Rai, Rachita,Deschamps, Jeffrey R.,Mackerell Jr., Alexander D.,Faden, Alan I.,Xue, Fengtian
, p. 842 - 844 (2014)
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.
