A method of producing an α,β-unsaturated dicarboxylic acid ester exemplified by an α-hydromuconic acid ester from a carboxylic acid ester exemplified by a 3-hydroxyadipic acid ester or a 3-hydroxyadipic acid-3,6-lactone ester, in which the selectivity for the α,β-unsaturated dicarboxylic acid ester can be increased by subjecting the carboxylic acid ester to a basic condition of pH 8.5 to less than 13 in an organic solvent or a mixed solvent of an organic solvent and water.

Described herein is a process for the preparation of a mixture of compounds of formula ##STR00001##
having a weight ratio of the cis-diastereomers to trans-diastereoisomers higher than 1:1, where R.sub.1 represents a C.sub.1-8 alkyl group, a C.sub.2-8 alkenyl group or a C.sub.2-8 alkynyl group, each optionally substituted with one or two of a C.sub.1-4 alkyl alkoxy ether group and/or a C.sub.1-4 alkyl carboxylester group and R.sub.2 represents a C.sub.1-6 alkyl, a C.sub.2-6 alkenyl or a C.sub.2-6 alkynyl group, each optionally substituted with a C.sub.1-4 alkyl alkoxy ether group, a carboxylic acid group or a C.sub.1-4 alkyl carboxylester group and compounds suitable in the process.

Described herein is a process for the preparation of a mixture of compounds of formula ##STR00001##
having a weight ratio of the cis-diastereomers to trans-diastereoisomers higher than 1:1, where R.sub.1 represents a C.sub.1-8 alkyl group, a C.sub.2-8 alkenyl group or a C.sub.2-8 alkynyl group, each optionally substituted with one or two of a C.sub.1-4 alkyl alkoxy ether group and/or a C.sub.1-4 alkyl carboxylester group and R.sub.2 represents a C.sub.1-6 alkyl, a C.sub.2-6 alkenyl or a C.sub.2-6 alkynyl group, each optionally substituted with a C.sub.1-4 alkyl alkoxy ether group, a carboxylic acid group or a C.sub.1-4 alkyl carboxylester group and compounds suitable in the process.

The present invention relates to a novel and improved process for preparing (3S)-3-(4-chloro-3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}phenyl)-3-cyclopropylpropanoic acid of the formula (I), to the compound of the formula (I) in crystalline form and to their use for the treatment and/or prevention of diseases, in particular for the treatment and/or prevention of cardiovascular, cardiopulmonary and cardiorenal disorders.

The present invention relates to a novel and improved process for preparing (3S)-3-(4-chloro-3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}phenyl)-3-cyclopropylpropanoic acid of the formula (I), to the compound of the formula (I) in crystalline form and to their use for the treatment and/or prevention of diseases, in particular for the treatment and/or prevention of cardiovascular, cardiopulmonary and cardiorenal disorders.

The present disclosure, in at least certain embodiments, is directed to shikimate (shikimic acid) analogues and compositions thereof, devices and kits which contain the shikimate analogues or compositions thereof, and methods of use of the compounds and compositions for treating and neutralizing irritant or odoriferous compounds on animate or inanimate surfaces or in atmospheres.

The present disclosure, in at least certain embodiments, is directed to shikimate (shikimic acid) analogues and compositions thereof, devices and kits which contain the shikimate analogues or compositions thereof, and methods of use of the compounds and compositions for treating and neutralizing irritant or odoriferous compounds on animate or inanimate surfaces or in atmospheres.

The present invention provides processes for preparing an α-necrodyl compound of the following general formula (3): wherein R.sup.2 represents a monovalent hydrocarbon group having 1 to 9 carbon atoms, the process comprising: subjecting a 3, 5, 5-trimethyl-3-cyclopentene compound of the following general formula (1): wherein R.sup.2 is as defined above, and X represents a leaving group, to a nucleophilic substitution reaction with a methylating agent of the following general formula (2): wherein M represents Li, MgZ.sup.1, ZnZ.sup.1, Cu, CuZ.sup.1, or CuLiZ.sup.1, and Z.sup.1 represents a halogen atom or a methyl group, to form the α-necrodyl compound (3). The present invention further provides processes for preparing γ-necrodyl compounds of the following general formula (4): wherein R.sup.2 represents a monovalent hydrocarbon group having 1 to 9 carbon atoms, the process comprising: subjecting the α-necrodyl compound (3) thus obtained to a positional isomerization reaction at the double bond to form the γ-necrodyl compound (4).

##STR00001##

The present invention provides processes for preparing an α-necrodyl compound of the following general formula (3): wherein R.sup.2 represents a monovalent hydrocarbon group having 1 to 9 carbon atoms, the process comprising: subjecting a 3, 5, 5-trimethyl-3-cyclopentene compound of the following general formula (1): wherein R.sup.2 is as defined above, and X represents a leaving group, to a nucleophilic substitution reaction with a methylating agent of the following general formula (2): wherein M represents Li, MgZ.sup.1, ZnZ.sup.1, Cu, CuZ.sup.1, or CuLiZ.sup.1, and Z.sup.1 represents a halogen atom or a methyl group, to form the α-necrodyl compound (3). The present invention further provides processes for preparing γ-necrodyl compounds of the following general formula (4): wherein R.sup.2 represents a monovalent hydrocarbon group having 1 to 9 carbon atoms, the process comprising: subjecting the α-necrodyl compound (3) thus obtained to a positional isomerization reaction at the double bond to form the γ-necrodyl compound (4).

##STR00001##

The present invention provides a process for preparing a compound of the following general formula (2): wherein R.sup.1 represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, and R.sup.3 represents a hydrogen atom or a methyl group, the process comprising: subjecting a compound of the following general formula (1): wherein R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, R.sup.3 represents a hydrogen atom or a methyl group, and the wavy bond represents an E-configuration, a Z-configuration, or a mixture thereof, to a Dieckmann condensation in the presence of base to form the compound (2).

##STR00001##