# US 5,347,042 A · Optically active sulphur-containing amino acid derivatives, their preparation, their polymerisation to give optically active polymers and the use thereof

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- Number: US 5,347,042 A
- Document ID: US5347042A
- Status: Granted
- Kind: A
- Application number: 07/897,196
- Filed: 1992-06-11
- Granted: 1994-09-13
- Earliest claimed: 1991-06-22
- Assignees: Bayer Aktiengesellschaft
- Inventors: Michael Grosse-Bley; Bruno Bomer; Rolf Grosser; Dieter Arlt; Walter Lange
- Web page: https://patentgrep.com/patent/US5347042A

## CPC

- C07C 323/60: with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
- C07C 323/59: with acylated amino groups bound to the carbon skeleton
- C07D 277/06: with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C08F 20/54: Amides {, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide}
- C07C 2601/14: The ring being saturated
- C07C 2602/42: the bicyclo ring system containing seven carbon atoms
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

The invention relates to new optically active sulphur-containing amino acid derivatives, a process for their preparation, their polymerisation to give optically active polymers and the use of these optically active polymers as adsorbents for chromatographic separation of racemates into enantiomers.

## Claims

### Claim 1

An optically active sulphur-containing amino acid derivative of the formula ##STR11## in which R represents hydrogen, methyl or fluorine,
R.sub.1 represents hydrogen or C.sub.1 -C.sub.4 -alkyl,
R.sub.2 represents a straight-chain, branched or cyclic alkyl radical having up to 10 C atoms, or phenyl
R.sub.3 represents a C.sub.10 -terpenyl radical, an adamantyl radical or a decahydronaphthyl radical, or represents a branched alkyl or cycloalkyl radical having from 2 to 20 C atoms, which is optionally mono-, di- or trisubstituted by halogen, alkoxy having 1 to 4 C atoms, or C.sub.3 -C.sub.12 -cycloalkyl, wherein the aryl and cycloalkyl radicals are optionally substituted by C.sub.1 -C.sub.4 -alkyl, and
A represents a methylene or dimethylene group which is optionally mono- or di-C.sub.1 -C.sub.4 -alkyl-substituted.

### Claim 2 (depends on 1)

A compound according to claim 1, in which
R represents hydrogen, methyl or fluorine,
R.sub.1 denotes hydrogen or methyl,
R.sub.2 represents alkyl having up to 8 C atoms or phenyl
R.sub.3 represents a C.sub.10 -terpenyl radical, an adamantyl radical or a decahydronaphthyl radical, or represents a branched alkyl or cycloalkyl radical having from 4 to 12 C atoms, which is optionally mono- or di-substituted by C.sub.6 -C.sub.10 -aryl, C.sub.1 -C.sub.4 -alkoxy, C.sub.3 -C.sub.12 -cycloalkyl or halogen, wherein the aryl and cycloalkyl radicals are optionally substituted by C.sub.1 -C.sub.4 -alkyl, and
A represents a methylene, dimethylmethylene, or dimethylene group.

### Claim 3 (depends on 1)

A compound according to claim 1 wherein A is ##STR12## and R.sub.2 is an alkyl or phenyl.

### Claim 4 (depends on 1)

A compound according to claim 1, in which R.sub.3 is tert-butyl or 3-pentyl.

### Claim 5 (depends on 1)

A compound according to claim 1 of the formula ##STR13##