# US 5,332,675 A · Optically active aromatic carboxylic acid derivatives and process for producing the same

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- Number: US 5,332,675 A
- Document ID: US5332675A
- Status: Granted
- Kind: A
- Application number: 07/920,159
- Filed: 1992-07-27
- Granted: 1994-07-26
- Earliest claimed: 1987-04-30
- Assignees: Sumitomo Chemical Company, Limited
- Inventors: Masayoshi Minai; Takayuki Higashii
- Web page: https://patentgrep.com/patent/US5332675A

## CPC

- C12P 7/42: Hydroxy-carboxylic acids
- C07C 65/24: polycyclic
- C07C 69/76: Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C12P 41/00: Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Disclosed are optically active aromatic carboxylic acid derivatives represented by the formula (I): ##STR1## (wherein R.sub.2 represents an alkoxyalkyl group having 1 to 20 carbon atoms or an alkyl group having 1 to 20 carbon atoms, which alkyl group may be substituted with a halogen atom; l represents a number of 1 or 2; m represents a number of 0 or 1; and * indicates asymmetric carbon atom) and a process for producing such derivatives through the following reaction steps: ##STR2## A process for the hydrolysis of ester derivatives of (I) using esterase is described. The optically active aromatic carboxylic acid derivatives represented by the above-described formula (I) are useful as a liquid crystal material and can be also utilized as an intermediate for the preparation of pharmaceuticals, agricultural chemicals and the like.

## Claims

### Claim 1

A process for preparing an optically active alcohol of the formula: ##STR26## (wherein R.sub.1 represents a lower alkyl group or ##STR27## wherein Z represents a hydrogen atom, a halogen atom or a lower alkyl or lower alkoxyl group; l represents a number of 1 or 2; and * indicates asymmetric carbon atom) comprising subjecting an ester represented by the formula: ##STR28## (wherein R.sub.1 and l are as defined above, and R" represents a lower alkyl group) to asymmetric hydrolysis by using an esterase having the ability to hydrolyze one of the enantiomers of said ester, said esterase being derived from an animal or a plant and selected from the group consisting of swine liver esterase, steapsin, pancreatin and wheat germ esterase.

### Claim 2 (depends on 1)

The process according to claim 1, wherein the asymmetric hydrolysis is carried out in a buffer solution.

### Claim 3 (depends on 1)

The process according to claim 1, wherein the asymmetric hydrolysis reaction temperature is 10.degree.-60.degree. C.

### Claim 4 (depends on 2)

The process according to claim 2, which is carried out in the presence of an organic solvent.

### Claim 5 (depends on 4)

The process according to claim 4, wherein the organic solvent is toluene, chloroform, methyl isobutyl ketone or dichloromethane.

### Claim 6

A process for producing an optically active alcohol of the formula: ##STR29## (wherein R.sub.1 represents a lower alkyl group or ##STR30## wherein Z represents a hydrogen atom, a halogen atom or a lower alkyl or lower alkoxyl group; l represents a number of 1 or 2; and * indicates asymmetric carbon atom) comprising:
subjecting an ester represented by the formula: ##STR31## (wherein R.sub.1 and l are as defined above, and R" represents a lower alkyl group to asymmetric hydrolysis by using an esterase having the ability to hydrolyze one of the enantiomers of said ester, said esterase being selected from the group consisting of Lipase P, Lipase AP, Lipase M-AP, Lipase MY, Lipase PL, Lipase AL, Lipase Godo BSL, lipase derived from the Chromobacterium, Talipase, and Lipase Saiken.

### Claim 7

A process for producing an optically active alcohol of the formula: ##STR32## wherein R.sub.1 represents a lower alkyl group or ##STR33## wherein Z represents a hydrogen atom, a halogen atom or a lower alkyl or lower alkoxyl group; l represents a number of 1 or 2; and * indicates asymmetric carbon atom, comprising:
subjecting an ester represented by the formula: ##STR34## wherein R.sub.1 and l are as defined above, and R" represents a lower alkyl group, to asymmetric hydrolysis by using an esterase having the ability to hydrolyze one of the enantiomers of said ester, said esterase being selected from the group consisting of lipase derived from the Pseudomonas, Lipase P, and lipase derived from the Arthrobactor, Lipase Godo BSL.

### Claim 8

An optically active alcohol represented by the formula: ##STR35## wherein R.sub.1 represents a lower alkyl group or ##STR36## wherein Z represents a hydrogen atom, a halogen atom or a lower alkyl or lower alkoxyl group; l is 1 or 2; and * indicates an asymmetric carbon atom, provided that when l=1, R.sub.1 is ##STR37##