4-5-dihydro-4-oxo-2-¬2-trans-phenylcyclopropyl)...

C - Chemistry – Metallurgy – 07 – D

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260/361.1

C07D 307/68 (2006.01)

Patent

CA 1240687

ABSTRACT Antimicrobial 4,5-dihydro-4-oxo-2-((2-trans-phenylcyclopropyl) amino]-3-furancarboxylic acids and derivatives thereof which have the formula: Image where R is selected from hydroxy, lower alkoxy, and O-alkali metal; and where R1 is selected from phenyl and phenyl substituted with lower alkyl and/or halogen. The invention further provides a process for the preparation of these compounds, characterized by preparing the ester derivatives, where R is lower alkoxy, by a base catalyzed cyclocondensation of a lower alkyl-4- chloroacetoacetate with a trans-phenylcyclopropyl isocyanate of the formula: Image where R1 is as defined above, preparing the free acid, where R is hydroxy, by alkaline hydrolysis of the ester derivatives, and preparing the salt derivatives, where R is O-alkali metal, by reaction of the free acid with an alkali metal carbonate.

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