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Carbamoyl Azides of α-N-Protected Amino Acids: A Fast and Simple One-Pot Synthesis
| Content Provider | Scilit |
|---|---|
| Author | Verardo, Giancarlo Bombardella, Elisa Geatti, Paola Strazzolini, Paolo |
| Copyright Year | 2008 |
| Description | 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 benzyloxycarbonyl (α-N-Cbz) protected proline afforded the corresponding isocyanates instead of the expected carbamoyl azides. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2008-1032029.pdf |
| Ending Page | 444 |
| Page Count | 7 |
| Starting Page | 438 |
| ISSN | 00397881 |
| e-ISSN | 1437210X |
| DOI | 10.1055/s-2008-1032029 |
| Journal | Synthesis |
| Issue Number | 3 |
| Volume Number | 2008 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2008-01-10 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synthesis Organic Chemistry Α-n-protected Amino Acids Sodium Azide Carbamoyl Azide Mixed Anhydride Curtius Rearrangement |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
