Green Synthesis of α,β- and β,β-Dipeptides under Solvent-Free Conditions

The reactivity of N-tert-butyloxycarbonyl-N-carboxyanhydrides derived from β-alanine, (S)-β3-homophenylglycine, and (S)-β3-carboxyhomoglycine with different α- and β-amino ester hydrochlorides was examined under ball-milling activation. In particular, good to excellent yields of several relevant α,β...

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Bibliographic Details
Published in:Journal of organic chemistry 2010-11, Vol.75 (21), p.7107-7111
Main Authors: Hernández, José G, Juaristi, Eusebio
Format: Article
Language:English
Subjects:
Alanine - chemistry
Chemical reactivity
Chemistry
Dipeptides - chemical synthesis
Dipeptides - chemistry
Esters
Exact sciences and technology
Glycine - chemistry
Green Chemistry Technology - methods
Models, Molecular
Molecular Conformation
Organic chemistry
Peptides
Preparations and properties
Reactivity and mechanisms
Stereoisomerism
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Summary:The reactivity of N-tert-butyloxycarbonyl-N-carboxyanhydrides derived from β-alanine, (S)-β3-homophenylglycine, and (S)-β3-carboxyhomoglycine with different α- and β-amino ester hydrochlorides was examined under ball-milling activation. In particular, good to excellent yields of several relevant α,β- and β,β-dipeptides were obtained. An illustrative application of this methodology consisted in the high-yield synthesis of the mammalian α,β-dipeptide N-Boc-l-carnosine-OMe.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo101159a