Synthesis of 5-substituted 5-hydroxy-2-pyrrolidones, metabolites of the antipsychotic benzamide remoxipride
| Autor: | Lars Gawell, Curt-Eric Hagberg, Thomas Högberg, Marianne Widman, Kjell Ankner, Ulf Junggren, Bo Lamm, Peter Nordberg, Magnus Erickson, Inger Grundevik, Inger Hagin, Kurt-Jürgen Hoffman, Svante Johansson, Sam Larsson, Ingalil Löfberg, Kristina Ohlson, Björn Persson, Inger Skånberg, Lija Tekenbergs-Hjelte |
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| Rok vydání: | 1989 |
| Předmět: |
General Chemical Engineering
Metabolite medicine.medical_treatment Antagonist Reference Standards Medicinal chemistry Pyrrolidinones chemistry.chemical_compound Ammonia chemistry Dopamine Benzamides Remoxipride medicine Humans Ethylamine Benzamide Antipsychotic Chromatography High Pressure Liquid medicine.drug Antipsychotic Agents |
| Zdroj: | Acta chemica Scandinavica (Copenhagen, Denmark : 1989). 43(5) |
| ISSN: | 0904-213X |
| Popis: | This paper describes the synthesis of 5-[(3-bromo-2,6-dimethoxybenzamido)-methyl]-5-hydroxy-2-pyrrolidon e (3) and its 1-ethyl analogue 2, two urinary metabolites of the dopamine D-2 antagonist remoxipride [1, (S)-3-bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2, 6-dimethoxybenzamide]. Two synthetic schemes leading to a common intermediate, 5-benzamido-4-oxopentanoic acid 4, were developed. This key intermediate permits conversion into either metabolite. Reaction of 4 with isobutyl chloroformate furnished a mixed carbonic anhydride, which upon treatment with ethylamine or ammonia gave the 4-oxopentanamides 5 and 6, respectively. Ring-closure afforded the corresponding 5-hydroxy-2-pyrrolidones 2 and 3. |
| Databáze: | OpenAIRE |
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