Premium
A New 2 H ‐Azirin‐3‐amine as a Synthon for α ‐Methyl Glutamate
Author(s) -
Hilty Florentine M.,
Brun Kathrin A.,
Heimgartner Heinz
Publication year - 2004
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490226
Subject(s) - synthon , chemistry , diastereomer , dipeptide , amine gas treating , stereochemistry , protecting group , block (permutation group theory) , side chain , amino acid , organic chemistry , biochemistry , alkyl , geometry , mathematics , polymer
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 ).