# US 5,703,234 A · Heterocyclic alkanamide

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- Number: US 5,703,234 A
- Document ID: US5703234A
- Status: Granted
- Kind: A
- Application number: 08/462,676
- Filed: 1995-06-05
- Granted: 1997-12-30
- Earliest claimed: 1993-06-23
- Assignees: Tanabe Seiyaku Co., Ltd.
- Inventors: Tameo Iwasaki; Kazuhiko Kondo; Hiroshi Ohmizu
- Web page: https://patentgrep.com/patent/US5703234A

## CPC

- C07D 205/085: with a nitrogen atom directly attached in position 3
- C07D 205/08: with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D 217/24: Oxygen atoms
- C07D 239/90: with acyclic radicals attached in position 2 or 3
- C07D 265/14: condensed with one six-membered ring
- C07D 265/22: Oxygen atoms
- C07D 279/14: condensed with carbocyclic rings or ring systems
- C07D 477/02: Preparation (by microbiological processes C12P17/18)
- C07D 477/04: by forming the ring or condensed ring systems
- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- C07F 7/1892: {by reactions not provided for in C07F7/1876 - C07F7/1888}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

Novel process for preparing azetidinone compound of the formula ›III!: ##STR1## wherein R.sup.1 is H or lower alkyl, R.sup.2 and R.sup.3 combine together with the adjacent nitrogen to form heterocyclic group, and R.sup.4 is protected or unprotected hydroxy-substituted lower alkyl, which comprises reacting an alkanamide compound of the formula ›I!: ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are the same as defined above, with a compound of the formula ›II!: ##STR3## wherein L.sup.1 is a leaving group and R.sup.4 is the same as defined above, in the presence of a base, said compound ›Ill! being useful as synthetic intermediate for 1-methylcarbapenem derivative having excellent antibacterial activity.

## Claims

### Claim 1

A compound of the formula (I-A): ##STR94## wherein R.sup.1 is a lower alkyl group, Ring B is a substituted or unsubstituted benzene ring, X is an oxygen atom or a sulfur atom, Y is an oxygen atom, a sulfur atom, or a protected or unprotected imino group, Z.sup.1 and Z.sup.2 are the same or different and each a substituted or unsubstituted alkyl group, or an aralkyl group, or both combine at the ends thereof to form a substituted or unsubstituted alkylene group having 4 to 7 carbon atoms.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein Y is an oxygen atom or a sulfur atom, Z.sup.1 and Z.sup.2 are the same or different and each a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or both combine at the ends thereof to form a substituted or unsubstituted alkylene group having 4 to 7 carbon atoms.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein Ring B is an unsubstituted benzene ring, X is an oxygen atom, Y is an oxygen atom, Z.sup.1 and Z.sup.2 are the same or different and each a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or both combine at the ends thereof to form an unsubstituted alkylene group having 4 to 7 carbon atoms .