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Aminosäuren, 16. Darstellung von N ‐Acyl‐2,3‐didehydro‐2‐aminocarbonsäureestern
Author(s) -
Effenberger Franz,
Kühlwein Jürgen,
Drauz Karlheinz
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301211
Subject(s) - chemistry , formamide , yield (engineering) , catalysis , decomposition , solvent , medicinal chemistry , reactivity (psychology) , organic chemistry , derivative (finance) , amino acid , acylation , medicine , materials science , alternative medicine , pathology , economics , financial economics , metallurgy , biochemistry
Amino Acids, 16. – Synthesis of N ‐Acyl‐2,3‐didehydro‐2‐amino Acid Esters [2]N ‐Acyl‐2,3‐didehydro‐2‐amino acid esters 3, 5, 7–12 , with a great variety of N ‐substituents, are obtained in good yields by the perrhenate‐catalyzed decomposition of methyl 2‐azido carboxylates 1 in organic solvents in the presence of the corresponding acyl chlorides 2 . By using methyl 2‐azidoisovalerate ( 1a ), the conditions (catalyst, solvent, temperature) for the reaction to give 3a were optimized. The reactivity of acyl chlorides can be strongly enhanced with equimolar amounts of dimethyl formamide, which allows a lowering of the decomposition temperature for this reaction. Under these mild reaction conditions also the unstable N ‐acyldehydroalanine derivative 5f can be obtained in good yield.