119288-71-0

Upstream product

• 119288-65-2 [3-Chloro-1-(4-methoxy-phenyl)-2-oxo-4-phenyl-azetidin-3-yl]-phosphonic acid diethyl ester 
• 67-64-1 acetone 
• 119288-68-5 [(3S,4S)-1-(4-Methoxy-phenyl)-2-oxo-4-phenyl-azetidin-3-yl]-phosphonic acid diethyl ester 

Relevant academic research and scientific papers

3-Methylidene-β-lactams as potential inhibitors of β-lactamases. Part 1: Synthesis of α-substituted derivatives from imines by Reformatzky reaction with chlorotrimethylsilane, silylation and Peterson olefination

A new variation of the Reformatzky reaction with use of I2/zinc and chlorotrimethylsilane in THF and a shortened work-up is described allowing the synthesis of a wide variety of substituted β-lactams 3 in fairly good yield. These lactams are silylated according to the Peterson reaction yielding by reactions with appropriate carbonyl compounds E/Z-mixtures of the substituted 3-methylidene β-lactams 7, 8 and 10. The isomers are separated by CC and completely characterized by spectroscopic methods, mainly 1H NMR spectroscopy. Condensation of the 3-formyl methylidene derivative 10 with amines or malonate yields the conjugated products 11, and from the isopropylidene derivative 6 the pyridinium sulfonate 14 is prepared via 12 and 13. All methylidene β-lactams are prepared as model compounds for studying their activity against β-lactamases and for elucidating the mechanism of action.

Cycloaddition Reactions of (Diethylphosphono)ketenes

Methyl- and chloro(diethylphosphono)ketenes were found to add to cyclopentadiene or imines in unusual manner in the certain cases.Some chemical conversions and the Horner-Wittig reaction of the cycloadducts were examined.