# US 5,705,636 A · Cyclohexene derivatives

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- Number: US 5,705,636 A
- Document ID: US5705636A
- Status: Granted
- Kind: A
- Application number: 08/570,820
- Filed: 1995-12-12
- Granted: 1998-01-06
- Earliest claimed: 1993-03-20
- Assignees: Glaxo Wellcome Inc.
- Inventors: Russell John Thomas; Stefano Biondi; Tino Rossi; Stefania Anna Contini
- Web page: https://patentgrep.com/patent/US5705636A

## CPC

- C07D 205/08: with one oxygen atom directly attached in position 2, e.g. beta-lactams
- Y02P 20/55: Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Compounds of the formula ##STR1## wherein R.sub.1 represents hydrogen or a nitrogen protecting group, useful as intermediates in the preparation of compounds having antibacterial activity.

## Claims

### Claim 1

Compounds of the general formula (I) ##STR7## wherein R.sub.1 represents hydrogen or a nitrogen protecting group.

### Claim 2 (depends on 1)

A compound of the general formula (Ia) ##STR8## wherein R.sub.1 has the meanings defined in claim 1.

### Claim 3 (depends on 1)

A compound as claimed in claim 1 wherein R.sub.1 is hydrogen or a nitrogen protecting group selected from tri(C.sub.1-6 alkyl)silyl, C.sub.1-4 alkylthio, C.sub.1-6 alkoxymethyl, benzyloxymethyl, p-methoxybenzloxymethyl or C.sub.1-6 alkylsilyloxymethyl.

### Claim 4 (depends on 1)

A compound as claimed claim 1 wherein the nitrogen protecting group R.sub.1 is tri(C.sub.1-6 alkyl)silyl.

### Claim 5

(-) Erythro-(4R)-4-›(3'S)-cyclohexen-3-yl!-azetidin-2-one.

### Claim 6

(4R)-1-t-Butyldimethylsilyl-4-›(3'S)-cyclohexen-3-yl!-azetidin-2-one.

### Claim 7 (depends on 2)

A compound as claimed in claim 2 wherein R.sub.1 is hydrogen or a nitrogen protecting group selected from tri(C.sub.1-6 alkyl)silyl, C.sub.1-4 alkythio, C.sub.1-6 alkoxymethyl, benzyloxmethyl, p-methoxybenzyloxymethyl or C.sub.1-6 alkylsilyloxymethyl.

### Claim 8 (depends on 2)

A compound as claimed in claim 2 wherein the nitrogen protecting group R.sub.1 is tri(C.sub.1-6 alkyl)silyl.

### Claim 9 (depends on 3)

A compound as claimed in claim 3 wherein the nitrogen protecting group R.sub.1 is tri(C.sub.1-6 alkyl)silyl.

### Claim 10 (depends on 1)

Compounds of claim 1 which comprise at least 50% of the (4R)(3'S) isomer (1a) ##STR9##

### Claim 11 (depends on 1)

Compounds of claim 1 which comprise at least 70% of the (4R)(3'S) isomer (1a) ##STR10##

### Claim 12 (depends on 1)

Compounds of claim 1 which comprise at least 85% of the (4R)(3'S) isomer (1a) ##STR11##

### Claim 13 (depends on 1)

Compounds of claim 1 which comprise at least 69% of the (4R)(3'S) isomer (1a) ##STR12##

### Claim 14 (depends on 1)

Compounds of claim 1 which comprise at least 87% of the (4R)(3'S) isomer (1a) ##STR13##