Hofmann rearrangement of primary carboxamides and cyclic imides using DCDMH and application to the synthesis of gabapentin and its potential peptide prodrugs
| Autor: | Jashuva V. P. Katuri, Kuppuswamy Nagarajan |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Primary (chemistry) Gabapentin 010405 organic chemistry Organic Chemistry Peptide Prodrug 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Amino acid Methyl carbamate chemistry.chemical_compound chemistry Drug Discovery Anthranilic acid medicine Hofmann rearrangement medicine.drug |
| Zdroj: | Tetrahedron Letters. 60:552-556 |
| ISSN: | 0040-4039 |
| Popis: | Two protocols for the efficient transformation of aromatic as well as aliphatic primary carboxamides to the corresponding carbamates and aromatic as well as aliphatic cyclic imides to the corresponding anthranilic acid derivatives & amino acid derivatives, respectively, are described. We also developed a novel methodology to the multigram scale synthesis of gabapentin and (S)-pregabalin. The gabapentin methyl carbamate was converted to novel potential peptide prodrugs of gabapentin. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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