1229693-88-2Relevant academic research and scientific papers
Ethyl 2-(tert-Butoxycarbonyloxyimino)-2-cyanoacetate (Boc-Oxyma): An Efficient Reagent for the Racemization Free Synthesis of Ureas, Carbamates and Thiocarbamates via Lossen Rearrangement
Manne, Srinivasa Rao,Thalluri, Kishore,Giri, Rajat Subhra,Chandra, Jyoti,Mandal, Bhubaneswar
, p. 168 - 176 (2017)
Boc-Oxyma (Ethyl 2-(tert-butoxycarbonyloxyimino)-2-cyanoacetate) has been reported previously as an efficient coupling reagent for the synthesis of amides, peptides, esters, thioesters and hydroxamic acids. It is known for its excellent racemization suppression capability, and also as an environment friendly reagent as it generates only Oxyma as solid byproduct that can be recovered easily and recycled for the synthesis of the same reagent. In this update, we report a simple, efficient, environment friendly, chemoselective and racemization free method for the synthesis of ureas, carbamates and thiocarbamates from hydroxamic acids via Lossen rearrangement by using Boc-Oxyma. We have achieved racemization free di- and tri-peptidyl ureas with very good yield by using this protocol. A rigorous mechanistic investigation is also incorporated. (Figure presented.).
Simple and mild one-pot synthesis of dipeptidyl ureas via carbamoyl azides of α-N-protected amino acids
Venneri, Cesare Daniele,Verardo, Giancarlo,Strazzolini, Paolo
, p. 1027 - 1041 (2011/04/25)
(Chemical Equation Presented) A simple and mild one-pot synthesis of potentially bioactive α-N-protected dipeptidyl ureas is reported. The procedure involves the reaction between the carbamoyl azide of an α-N-protected amino acid and an α-amino acid methyl ester. The reaction is fast (3 h at 45 °C), regardless of the nature of both the reagents, and racemization free. The reported protocol represents a valid alternative to existing methods. Copyright Taylor & Francis Group, LLC.
T3P (propylphosphonic anhydride) mediated conversion of carboxylic acids into acid azides and one-pot synthesis of ureidopeptides
Basavaprabhu,Narendra,Lamani, Ravi S.,Sureshbabu, Vommina V.
experimental part, p. 3002 - 3005 (2010/07/10)
A general, mild, efficient, and environmentally benign protocol, which makes use of T3P as an acid activating agent for the direct synthesis of acid azides from carboxylic acids is described. Further, the protocol is employed for the one-pot synthesis of α-ureidopeptides starting from N-protected α-amino acids.
