Carbamoyl Azides of α-N-Protected Amino Acids: A Fast and Simple One-Pot Synthesis
| Autor: | Paolo Strazzolini, Elisa Bombardella, Paola Geatti, Giancarlo Verardo |
|---|---|
| Rok vydání: | 2008 |
| Předmět: |
chemistry.chemical_classification
α-N-protected amino acids Carbamoyl azide Curtius rearrangement Mixed anhydride Sodium azide Sodium azide α-N-protected amino acids Carbamoyl azide Mixed anhydride Organic Chemistry One-pot synthesis Curtius rearrangement Medicinal chemistry Catalysis Amino acid Reaction rate chemistry.chemical_compound chemistry Amino acid side chain Proline Isobutyl chloroformate |
| Zdroj: | Synthesis. 2008:438-444 |
| ISSN: | 1437-210X 0039-7881 |
| DOI: | 10.1055/s-2008-1032029 |
| Popis: | 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 KH 2 PO 4 . 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 benzyl-oxycarbonyl (α- N-Cbz) protected proline afforded the corresponding isocyanates instead of the expected carbamoyl azides. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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