| alpha-Amidoalkylating agents from N-acyl-alpha-amino acids: 1-(N-acylamino)alkyltriphenylphosphonium salts. | |
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MedLine Citation:
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PMID: 22250978 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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N-Acyl-alpha-amino acids were efficiently transformed in a two-step procedure into 1-N-(acylamino)alkyltriphenylphosphonium salts - new powerful alpha-amidoalkylating agents. The effect of the alpha-amino acid structure, the base used [MeONa, or a silica gel-supported piperidine (SiO2-Pip)], and the main electrolysis parameters (current density, charge consumption) on the yield and selectivity of the electrochemical decarboxylative alpha-methoxylation of N acyl-alpha-amino acids (Hofer-Moest reaction) was investigated. For most proteinogenic and all studied unproteinogenic alpha-amino acids, very good results were obtained using a substoichiometric amount of SiO2-Pip as the base. Only in the case of N acylated cysteine, methionine and tryptophan attempts to carry out the Hofer-Moest reaction in the applied conditions failed, probably because of the susceptibility of these alpha-amino acids to an electrochemical oxidation. The methoxy group of N (1 methoxyalkyl)amides was effectively displaced with the triphenylphosphonium group by dissolving an equimolar amount of N (1-methoxyalkyl)amide and triphenylphosphonium tetrafluoroborate in CH2Cl2 at room temperature for 30 minutes, followed by the precipitation of 1-N-(acylamino)alkyltriphenylphosphonium salt with Et2O. |
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Authors:
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Roman Mazurkiewicz; Jakub Adamek; Agnieszka Październiok-Holewa; Katarzyna Zielińska; Wojciech Simka; Anna Gajos; Karol Szymura |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-1-16 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: - ISSN: 1520-6904 ISO Abbreviation: - Publication Date: 2012 Jan |
Date Detail:
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Created Date: 2012-1-18 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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