88367-37-7

Upstream product

• 64282-66-2 9-O-methylclavulanic acid 
• 88367-34-4 (Z)-(5R)-3-(p-chlorophenylseleno)-2-(2-methoxyethylidene)clavam 
• 75388-26-0 (E/Z)-(5R)-3-(2-methoxyethylidene)-4-oxa-1-azabicyclo<3.2.0>heptan-7-one 
• 93680-57-0 (Z)-(5R)-3-hydroxy-2-(2-methoxyethylidene)clavam 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 

Relevant academic research and scientific papers

Oxidative Decarboxylation of Clavulanic Acid and Its 9-Methyl Ether

The carboxy group of clavulanic acid has been replaced by a methoxy group, an acetoxy group, and a m-chlorobenzoyloxy group using standard methods for oxidative decarboxylation (electrolysis, reaction with lead tetra-acetate, and decarboxylative rearrangement of a diacyl peroxide, respectively).In an unexpected reaction, 9-O-methylclavulanic acid (20) reacted with p-chlorophenylselenenyl bromide and base to give 3-(p-chlorophenylseleno)-2-(2-methoxyethylidene)clavam (21).Refluxing a solution of compound (21) in toluene gave 3-hydroxy-2-(2-methoxyethylidene)clavam and b is(p-chlorophenyl)diselenide, the overall result being the replacement of the carboxy group in the acid (20) by a hydroxy group.In chloroform, this 3-hydroxyclavam exists predominantly as the ring-opened aldehyde.Possible mechanisms for the formation of the seleno derivative (21) and its decomposition in refluxing toluene are discussed.