71916-37-5

Basic information

• Product Name: (Z)-(3S,5R)-2-(2-hydroxyethylidene)-3-(m-chlorobenzoyloxy)clavam
• Synonyms: (Z)-(3S,5R)-2-(2-hydroxyethylidene)-3-(m-chlorobenzoyloxy)clavam
• CAS NO: 71916-37-5
• Molecular Weight: 309.706
• Mol File: 71916-37-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (Z)-(3S,5R)-2-(2-hydroxyethylidene)-3-(m-chlorobenzoyloxy)clavam(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-(3S,5R)-2-(2-hydroxyethylidene)-3-(m-chlorobenzoyloxy)clavam(71916-37-5)
• EPA Substance Registry System: (Z)-(3S,5R)-2-(2-hydroxyethylidene)-3-(m-chlorobenzoyloxy)clavam(71916-37-5)

Safety Data

• Hazardous Substances Data: 71916-37-5(Hazardous Substances Data)

Upstream product

• 937-14-4 3-chloro-benzenecarboperoxoic acid 
• 58001-44-8 clavulanic acid 

Downstream Products

• 71916-38-6 (Z)-(3S,5R)-3-(m-chlorobenzoyloxy)-2-(2-phenylacetoxyethylidene)clavam 

Relevant articles and documents

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The carboxy group of clavulanic acid has been replaced by a methoxy group, an acetoxy group, and a m-chlorobenzoyloxy group using standard methods for oxidative decarboxylation (electrolysis, reaction with lead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.