Synthesis of 2-methyl-5-amino-4-oxo-3-sulfonyl esters as precursors of pseudodipeptides |
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Authors: | Severi D. Ettouati L. Paris J. |
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Affiliation: | (1) Institut des Sciences Pharmaceutiques et Biologiques, Laboratoire de Chimie thérapeutique EA 635, Université Claude Bernard Lyon 1, 8 avenue Rockefeller, F-69373 Lyon cedex 08, France |
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Abstract: | Summary 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. |
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Keywords: | β -ketosulfone carba isostere E-alkene isostere 2-methyl-5-amino-4-oxo-3-sulfonyl esters ketomethylene isostere |
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