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A New 2H-Azirin-3-amine as a Synthon for α-Methyl Glutamate


Hilty, Florentine M; Brun, Kathrin A; Heimgartner, Heinz (2004). A New 2H-Azirin-3-amine as a Synthon for α-Methyl Glutamate. Helvetica Chimica Acta, 87(10):2539-2548.

Abstract

The synthesis of a novel 2,2-disubstituted 2H-azirin-3-amine 10 as a building block for racemic Glu(2Me) is described. This synthon contains an ester group in the side chain. The reaction of 10 with thiobenzoic S-acid and the amino acid Z-Val-OH yielded the racemic monothiodiamide 17 and the dipeptide 18 as a mixture of diastereoisomers, respectively (Scheme 2). From 18, each of the protecting groups was removed selectively (Scheme 3).

Abstract

The synthesis of a novel 2,2-disubstituted 2H-azirin-3-amine 10 as a building block for racemic Glu(2Me) is described. This synthon contains an ester group in the side chain. The reaction of 10 with thiobenzoic S-acid and the amino acid Z-Val-OH yielded the racemic monothiodiamide 17 and the dipeptide 18 as a mixture of diastereoisomers, respectively (Scheme 2). From 18, each of the protecting groups was removed selectively (Scheme 3).

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2004
Deposited On:13 Aug 2013 15:03
Last Modified:05 Apr 2016 16:54
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, Stiftung für wissenschaftliche Forschung an der Universität Zürich, Prof. Dr. Hans E. Schmid-Stiftung
Publisher DOI:https://doi.org/10.1002/hlca.200490226

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