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

✍ Scribed by Florentine M. Hilty; Kathrin A. Brun; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
220 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The synthesis of a novel 2,2‐disubstituted 2__H__‐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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## 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 monothiodia

A Novel 2H-Azirin-3-amine as a Dipeptide
A Novel 2H-Azirin-3-amine as a Dipeptide (Aib-Hyp) Synthon
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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