1020082-40-9Relevant academic research and scientific papers
Study of the reaction between carbamoyl azides of α-N-protected amino acids and hydrazine monohydrate
Verardo, Giancarlo,Venneri, Cesare Daniele,Esposito, Gennaro,Strazzolini, Paolo
experimental part, p. 1376 - 1384 (2011/04/17)
Two simple and efficient synthetic methods for the preparation of semicarbazide amino acid derivatives are reported. The procedures involve reaction between the carbamoyl azides of α-N-protected amino acids and hydrazine monohydrate: 4-[(alkoxycarbonylamino)(alkyl)methyl]semicarbazides 1 are obtained when hydrazine is added to the separated tetrahydrofuran (THF) solution containing the carbamoyl azide at 0 °C, whereas 1-[(alkoxycarbonylamino)(alkyl)methyl-carbamoyl]-4-[(alkoxycarbonylamino)(alkyl) methyl]semicarbazides 4 are produced by adding hydrazine directly into the final THF/aqueous buffer (KH2PO4) biphasic mixture containing the prepared carbamoyl azide at 50 °C, respectively. NMR experimental data obtained from samples dissolved in [D6]dimethyl sulfoxide suggest a dimeric association for semicarbazides 4 with intermolecular hydrogen bonds. Moreover, the ESI-MS-MS spectra reveal some interesting common features.
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
experimental part, 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.
Carbamoyl azides of α-N-protected amino acids: A fast and simple one-pot synthesis
Verardo, Giancarlo,Bombardella, Elisa,Geatti, Paola,Strazzolini, Paolo
, p. 438 - 444 (2008/09/20)
A fast and simple one-pot synthesis of carbamoyl azides of α-N-protected amino acids is reported. The procedure involves the reaction between sodium azide and the mixed anhydride obtained from an α-N-protected amino acid and isobutyl chloroformate, in the presence of KH2PO4. The reaction rate was influenced by the nature of both the α-N-protection and the amino acid side chain. Surprisingly, tert-butyloxycarbonyl (α-N-Boc) and benzyloxycarbonyl (α-N-Cbz) protected proline afforded the corresponding isocyanates instead of the expected carbamoyl azides. Georg Thieme Verlag Stuttgart.
