Synthesis of 2-methyl-5-amino-4-oxo-3-sulfonyl esters as precursors of pseudodipeptides

Delphine Severi (1) , Laurent Ettouati (1) , Joëlle Paris (1)

1 Synthèse organique de molécules bioactives

The synthesis of 2-methyl-5-amino-4-oxo-3-sulfonyl esters, potential precursors of XaaΨ[COCH2]Ala, XaaΨ[E-CH=CH]Ala and XaaΨ[CH2CH2]Ala pseudodipeptides, has been investigated by alkylation of aminoacid-derived β-ketosulfones with ethyl 2-bromo- or 2-triflyloxypropionate in different basic conditions. Yields in 2-methyl-5-amino-4-oxo-3-sulfonyl esters are low but starting β-ketosulfones are recovered in good yield

Mots clés: β-ketosulfone carba isostere E-alkene isostere 2-methyl-5-amino-4-oxo-3-sulfonyl esters ketomethylene isostere

Domaines: Médicaments; Chimie thérapeutique

Delphine Severi, Laurent Ettouati, Joëlle Paris. Synthesis of 2-methyl-5-amino-4-oxo-3-sulfonyl esters as precursors of pseudodipeptides. Letters in Peptide Science, 2002, 9 (1), pp.11 - 14. ⟨10.1007/BF02538302⟩. ⟨hal-01710026⟩