A Convenient and Scalable Synthesis of Ethyl N-[(2-Boc-amino)ethyl]glycinate and Its Hydrochloride. Key Intermediates for Peptide Nucleic Acid Synthesis

An improved synthesis of ethyl N-[(2-Boc-amino)ethyl]glycinate and its hydrochloride salt is reported. The synthesis is based on the reductive alkylation of Boc-ethylenediamine with ethyl glyoxylate hydrate and furnishes the title compound in near quantitative yield and high purity without chromatog...

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Veröffentlicht in:	Journal of organic chemistry 2003-02, Vol.68 (4), p.1630-1632
Hauptverfasser:	Viirre, Russell D, Hudson, Robert H. E
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkylation Catalysis Chemistry Chromatography Exact sciences and technology Glycine - analogs & derivatives Glycine - chemical synthesis Glycine - chemistry Indicators and Reagents Magnetic Resonance Spectroscopy Molecular Structure Organic chemistry Oxidation-Reduction Peptide Nucleic Acids - chemical synthesis Peptide Nucleic Acids - chemistry Peptides Preparations and properties
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Zusammenfassung:	An improved synthesis of ethyl N-[(2-Boc-amino)ethyl]glycinate and its hydrochloride salt is reported. The synthesis is based on the reductive alkylation of Boc-ethylenediamine with ethyl glyoxylate hydrate and furnishes the title compound in near quantitative yield and high purity without chromatography. This compound is suitable, as is, for the synthesis peptide nucleic acid monomers. Further, conversion to the hydrochloride salt provides a stable, nonhygroscopic solid that is a convenient form for handling and storage.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo026590w