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A new 2H-Azirin-3-amine as a synthon for 2-Methylaspartate


Brun, Kathrin A; Heimgartner, Heinz (2005). A new 2H-Azirin-3-amine as a synthon for 2-Methylaspartate. Helvetica Chimica Acta, 88(11):2951-2959.

Abstract

The synthesis of a novel 2,2-disubstituted 2H-azirin-3-amine 3a as a building block for racemic Asp(2Me) is described. This synthon contains an ester group in the side chain. The reaction of 3a with thiobenzoic acid and the amino acid Z-Val-OH yielded the racemic monothiodiamide 10a and the dipeptide 11 as a mixture of diastereoisomers, respectively (Scheme 2). In 11, each of the protecting groups was removed selectively (Scheme 3). First attempts toward the preparation of enantiomerically pure synthons for Asp(2Me) with a chiral auxiliary group in the side chain are described. Synthons 3b with a 1-(naphthalen-1-yl)ethyl ester group and 3c with a menthyl ester group were prepared and reacted with thiobenzoic acid to form monothiodiamides 10b and 10c (Scheme 2). However, the diastereoisomers of the synthons 3b and 3c could not be separated by chromatography.

Abstract

The synthesis of a novel 2,2-disubstituted 2H-azirin-3-amine 3a as a building block for racemic Asp(2Me) is described. This synthon contains an ester group in the side chain. The reaction of 3a with thiobenzoic acid and the amino acid Z-Val-OH yielded the racemic monothiodiamide 10a and the dipeptide 11 as a mixture of diastereoisomers, respectively (Scheme 2). In 11, each of the protecting groups was removed selectively (Scheme 3). First attempts toward the preparation of enantiomerically pure synthons for Asp(2Me) with a chiral auxiliary group in the side chain are described. Synthons 3b with a 1-(naphthalen-1-yl)ethyl ester group and 3c with a menthyl ester group were prepared and reacted with thiobenzoic acid to form monothiodiamides 10b and 10c (Scheme 2). However, the diastereoisomers of the synthons 3b and 3c could not be separated by chromatography.

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Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2005
Deposited On:23 Aug 2012 11:05
Last Modified:21 Nov 2017 16:08
Publisher:Verlag Helvetica Chimica Acta
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.200590238

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