# US 4,391,980 A · Aryloxymethyl oxazolinium derivatives

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- Number: US 4,391,980 A
- Document ID: US4391980A
- Status: Granted
- Kind: A
- Application number: 06/262,145
- Filed: 1981-05-11
- Granted: 1983-07-05
- Earliest claimed: 1978-07-28
- Assignees: Ciba-Geigy Corporation
- Inventors: Janos Zergenyi
- Web page: https://patentgrep.com/patent/US4391980A

## CPC

- C07D 263/14: with radicals substituted by oxygen atoms
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The invention relates to a process for inverting the configuration in optically active compounds of the formula ##STR1## in which Ar.sub.1 represents a monocyclic or polycyclic, carbocyclic or heterocyclic radical that has at least one ring of aromatic character and is bonded to the oxygen atom by way of a ring carbon atom, preferably of the ring of aromatic character, and R.sub.1 represents an optionally substituted aliphatic, cycloaliphatic or araliphatic hydrocarbon radical, or the salts thereof, characterized in that an optically active compound of the formula ##STR2## having a R(+) or S(-) configuration, in which R.sub.2 represents a monocyclic or polycyclic, carbocyclic or heterocyclic radical, or an optionally substituted aliphatic, cycloaliphatic or araliphatic hydrocarbon radical, is converted, by treating with a strong oxygen-containing inorganic or organic acid or halides thereof, into an optically active compound of the formula ##STR3## in which x.sup..crclbar. represents the anion of a strong, oxygen-containing inorganic or organic acid or of a halogen atom and the resulting compound of the formula III is hydrolyzed, optionally by way of the corresponding free base as intermediate, to form a compound of the formula I of a configuration opposite to that of the starting material used and, if desired, a free compound of the formula I is converted into a salt or a resulting salt is converted into the free compound.

## Claims

### Claim 1

An optically active compound of the formula ##STR8## wherein X.sup..crclbar. represents the anion of chlorine or bromine, or of sulfuric or phosphoric acid,
Ar.sub.1 represents 1-naphthyl, 3-lower alkylphenyl, 2-lower alkenylphenyl, 2-lower alkenyloxyphenyl, 4-lower alkanoylaminophenyl, 4-(2-lower alkoxyethyl)-phenyl, benzyloxyphenyl or hydroxyphenyl,
R.sub.1 represents lower alkyl, phenyl-lower alkyl or phenoxy-lower alkyl, and
R.sub.2 represents lower alkyl, phenyl-lower alkyl or phenyl.

### Claim 2 (depends on 1)

A compound as claimed in claim 1 wherein
X.sup..crclbar. represents the anion of chlorine or bromine, or of sulphuric or phosphoric acid,
Ar.sub.1 represents 1-naphthyl, 3-methylphenyl, 2-allylphenyl, 2-allyloxyphenyl, 4-acetylaminophenyl, 4-benzyloxyphenyl or 4-hydroxyphenyl,
R.sub.1 represents lower alkyl or phenyl-lower alkyl and
R.sub.2 represents lower alkyl, phenyl-lower alkyl or phenyl.

### Claim 3 (depends on 1)

A compound as claimed in claim 1 wherein
X.sup..crclbar. represents the anion of chlorine or sulphuric acid,
Ar.sub.1 represents 1-naphthyl, 2-allylphenyl, 2-allyloxyphenyl, 4-benzoyloxyphenyl or 4-hydroxyphenyl,
R.sub.1 represents lower alkyl and
R.sub.2 represents lower alkyl or phenyl.

### Claim 4 (depends on 1)

A compound as claimed in claim 1 which is S(-)-1-isopropyl-2-methyl-5-(4-benzyloxyphenoxymethyl)-oxazolinium chloride.

### Claim 5 (depends on 1)

A compound as claimed in claim 1 which is R(+)-1-isopropyl-2-methyl-5-(4-hydroxyphenoxymethyl)-oxazolinium sulphate.

### Claim 6 (depends on 1)

A compound as claimed in claim 1 which is L(-)-1-isopropyl-2-methyl-5-(o-allyloxyphenoxymethyl)-oxazolinium chloride.

### Claim 7 (depends on 1)

A compound as claimed in claim 1 which is (+)-1-isopropyl-2-methyl-5-[1-naphthyloxymethyl]-oxazolinium chloride.