79007-05-9

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 100-52-7 benzaldehyde 
• 93681-34-6 N-(α-methyl-β-mehoxycarbonylvinyl)aminoacetic acid potassium salt 
• 71703-43-0 (3,4-Dimethoxy-benzyl)-[1-phenyl-meth-(Z)-ylidene]-amine 
• 5763-61-1 3,4-dimethoxybenzylamine 

Downstream Products

• 71703-45-2 1-(3',4'-dimethoxy benzyl)-3-phenoxyacetamido-4-phenyl-azetidin-2-one 
• 79007-02-6 N-[(3S,4R)-1-(3,4-Dimethoxy-benzyl)-2-oxo-4-phenyl-azetidin-3-yl]-2-phenyl-acetamide 
• 30419-00-2 3-phenylacetamido-4-phenylazetidin-2-one 
• 71703-48-5 cis-3-Phenoxyacetylamino-4-phenyl-2-azetidinone 
• 71703-46-3 1-(3',4'-dimethoxy benzyl)-3-amino-4-phenylazetidin-2-one 

Relevant academic research and scientific papers

Synthesis of β-lactams from acetic acids and imines induced by phenyl dichlorophosphate reagent

The development of a practical method for the preparation of vinylamino-β-lactams from Dane salts and Schiff bases is described. Among the reagents known to produce β-lactams from imines and acetic acids, only phenyl dichlorophosphate and 1-methyl-2-chloropyridinium iodide are suitable for the synthesis of vinylamino-β-lactams. Reaction of acetic acids with ethanolimine derivatives promoted by phenyl dichlorophosphate affords oxazolidines instead of β-lactams. Protection of the hydroxyl group as the trimethylsilyl ether in the starting Schiff bases provides a convenient route to the corresponding β-lactams instead of oxazolidines. Some observations on the scope of the method are made.