Fast and Convenient Synthesis of α-N-Protected Amino Acid Hydrazides
| Autor: | Barbara Lesa, Paola Geatti, Giancarlo Verardo |
|---|---|
| Rok vydání: | 2004 |
| Předmět: |
chemistry.chemical_classification
Methylhydrazine Organic Chemistry Significant difference Regioselectivity Hydrazides Catalysis Anhydrides Amino acid chemistry.chemical_compound chemistry Amino acids Organic chemistry Ethyl chloroformate Reactivity (chemistry) Amino acids Anhydrides Hydrazides Protecting groups Regioselectivity Selectivity Protecting groups Phenylhydrazine |
| Zdroj: | Synthesis. 2005:559-564 |
| ISSN: | 1437-210X 0039-7881 |
| DOI: | 10.1055/s-2004-837300 |
| Popis: | A fast, simple and convenient synthesis of α-N-protected amino acid hydrazides is reported. The procedure involves the reaction between hydrazine monohydrate and the mixed anhydride obtained from an α-N-protected amino acid and ethyl chloroformate. When methylhydrazine was used, the reaction showed a good selectivity, yielding a mixture of 1-acyl-l-methylhydrazine and 1-acyl-2-methylhydrazine in a ratio 87:13. In contrast, when the reaction was carried out with phenylhydrazine, only 1 -acyl-2-phenylhydrazine was obtained. No significant difference in reactivity was observed with the different amino acids and N-protection introduced. |
| Databáze: | OpenAIRE |
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