Process for the catalytic preparation of N-acylglycine derivatives
OwnerHolger Geissler, Sandra Bogdanovic +3inventors
InventorsHolger Geissler, Sandra Bogdanovic, Matthias Beller, Markus Eckert, Frank Vollmuller
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Abstract
The present invention relates to a process for the catalytic preparation of N-acylglycine derivatives. More particularly, the present invention relates to a process for the catalytic preparation of N-acylglycine derivatives by reacting an aldehyde with a carboxamide and carbon monoxide in the presence of a palladium compound, an ionic halide and an acid as catalyst.
Claims24
A process for preparing N-acylglycine derivatives of the formula (III)
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- where
- R is hydrogen, a carboxyl group, a saturated, straight-chain, branched or cyclic (C1-C10)alkyl radical, a monounsaturated or polyunsaturated, straight-chain, branched or cyclic (C2-C10)alkenyl radical, a (C6-C18)aryl radical, a (C6-C18)heteroaryl radical, a (C1-C10)alkyl-(C6-C18)aryl radical, a (C1-C10)alkyl-(C6-C18)heteroaryl radical or a monounsaturated or polyunsaturated (C2-C10)alkenyl-(C6-C18)aryl radical, where one or more radicals —CH2— can be replaced by C═O or —O—,
- R′ is hydrogen, a saturated, straight-chain, branched or cyclic (C1-C26)alkyl radical, a monounsaturated or polyunsaturated, straight-chain, branched or cyclic (C2-C24)alkenyl radical, a (C6-C18)aryl radical, a (C1-C10)alkyl-(C6-C18)aryl radical or a monounsaturated or polyunsaturated (C2-C10)alkenyl-(C6-C18)aryl radical and
- R″ is hydrogen, a saturated, straight-chain, branched or cyclic (C1-C26)alkyl radical, a monounsaturated or polyunsaturated, straight-chain, branched or cyclic (C2-C23)alkenyl radical, a (C6-C18)aryl radical, a (C1-C10)alkyl-(C6-C18)aryl radical or a monounsaturated or polyunsaturated (C2-C10)alkenyl-(C6-C18)aryl radical,
- where R, R′ and R″ may be substituted,
- which comprises carbonylating a carboxamide of the formula (II)
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- where R′ and R″ are as defined above, together with an aldehyde of the formula RCHO, where R is as defined above, in the presence of a solvent, a palladium compound, an ionic halide and an acid as catalyst at a temperature of 20-200° C. and a CO pressure of 1-150 bar.
The process as claimed in any of the preceding claims, wherein the compounds of the formula (II) are used as mixtures as are obtainable from natural products.
The process as claimed in any of the preceding claims, wherein the aldehyde of the formula (I) is selected from the group consisting of formaldehyde, acetaldehyde, benzaldehyde, furfural, propionaldehyde, butyraldehyde, glyoxalic acid and isobutyraldehyde.
The process as claimed in any of the preceding claims, wherein the aldehyde is used in the form of its trimers or oligomers.
The process as claimed in any of the preceding claims, wherein the aldehyde is used in an amount of from 70 to 200 mol %, based on the carboxamide.
The process as claimed in any of the preceding claims, wherein the palladium compound is selected from the group consisting of palladium(0) compounds, palladium(II) compounds and palladium-phosphine complexes.
The process as claimed in any of the preceding claims, wherein the solvent used contains product up to the saturation limit.
The process as claimed in any of the preceding claims, wherein the reaction is carried out at pressures of from 1 to 150 bar and at temperatures of from 20 to 200° C.
Dependencies are inferred from the claim text.