Synthesis of 6-exomethylenepenams as beta-lactamase inhibitors

C Im; J S Oh; C B Yim

doi:10.1007/BF02976438

Synthesis of 6-exomethylenepenams as beta-lactamase inhibitors

Arch Pharm Res. 1999 Feb;22(1):68-71. doi: 10.1007/BF02976438.

Authors

C Im¹, J S Oh, C B Yim

Affiliation

¹ College of Pharmacy, Chung-Ang University, Seoul, Korea.

PMID: 10071962
DOI: 10.1007/BF02976438

Abstract

The 6,6-dibromopenam (6) was treated with CH3MgBr and carbaldehyde 5 to afford the hydroxy compound 7, which was reacted with acetic anhydride to give acetoxy compound 8. The deacetobromination of 8 with zinc and acetic acid gave 6-exomethylenepenams, E-isomer 10 and Z-isomer 9, which was oxidized to sulfone 11 by m-CPBA. The p-methoxybenzyl compounds were deprotected by AlCl3 and neutralized to give the sodium salts 12, 13 and 14.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Chromatography, Thin Layer
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / chemistry
Magnetic Resonance Spectroscopy
Penicillins / chemical synthesis*
Penicillins / chemistry
Spectrophotometry, Ultraviolet
beta-Lactamase Inhibitors*

Substances

Enzyme Inhibitors
Penicillins
beta-Lactamase Inhibitors