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US 6,835,851 B2Granted
Process for synthesizing N-(mercaptoacyl) amino acid derivatives from alpha-substituted acrylic acids
AssigneeBioprojet
InventorsThierry Monteil, Denis Danvy, Jean-Christophe Plaquevent, Pierre Duhamel, Lucette Duhamel, Jeanne-Marie Lecomte, Jean-Charles Schwartz, Serge Piettre
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Abstract
The instant invention relates to a process for preparing a compound of formula (I): said process comprising a step (B) which consists in performing a Michael addition of a thioacid RS4H on to an α-substituted acrylamide derivative. The invention also relates to the enantioselective synthesis of compounds of formula (I) wherein R2 is other than H, in the preferential (S, S) configuration:
Claims17
A process for preparing a compound of formula (I):
- wherein:
- R1 represents:
- a phenyl group;
- or
- a 3,4-methylenedioxyphenyl group;
- R2 represents a hydrogen atom or a lower alkyl group;
- R3 represents a lower alkyl group or a lower phenylalkylene group;
- and
- R4 represents a linear or branched aliphatic acyl radical or an aromatic acyl radical,
- said process comprising step (B) performing a Michaël addition of a thioacid of formula (IV):
- R4SH (IV)
- wherein R4 has the same meaning as in formula (I),
- with an α-substituted acrylamide derivative of formula (V):
- wherein R1, R2 and R3 have the same meaning as in formula (I).
11 more elements
A process for preparing a compound of formula (I):
- wherein:
- R1 represents:
- a phenyl group;
- or
- a 3,4-methylenedioxyphenyl group;
- R2 represents a hydrogen atom or a lower alkyl group;
- R3 represents a lower alkyl group or a lower phenylalkylene group;
- and
- R4 represents a linear or branched aliphatic acyl radical or an aromatic acyl radical,
- said process comprising step (B) performing a Michaël addition a thioacid of formula (IV):
- R4SH (IV)
- wherein R4 has the same meaning as in formula (I),
- with an α-substituted acrylamide derivative of formula (V):
- wherein R1 and R2 have the same meaning as in formula (I), R3 denotes a lower alkyl groups, said compound (V) being used at least predominantly in its S configuration or at least predominantly in its R configuration, and
- wherein quinquina alkaloid or derivatives thereof are used in step (B).
12 more elements
Dependencies are inferred from the claim text.