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A New 2H-Azirin-3-amine as a Synthon for 2-Methylaspartate

✍ Scribed by Kathrin A. Brun; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
2005
Tongue
German
Weight
130 KB
Volume
88
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The synthesis of a novel 2,2‐disubstituted 2__H__‐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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A Novel 2H-Azirin-3-amine as a Dipeptide
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The synthesis of methyl (2S,4R)-4-(benzyloxy)-N-(2,2-dimethyl-2H-azirin-3-yl)prolinate ( 10), a novel 2Hazirin-3-amine (3-amino-2H-azirine), is described (Scheme 1). The reaction of methyl (2S,4R)-N-(2methylpropanoyl)-4-(benzyloxy)prolinate ( 7) with Lawesson reagent gave methyl (2S,4R)-4-(benzyloxy