90475-32-4

Basic information

• Product Name: 2-Azetidinone, 4-(4-chlorophenyl)-1-(4-methoxyphenyl)-
• CAS NO: 90475-32-4
• Molecular Formula: C16H14ClNO2
• Molecular Weight: 287.746
• Mol File: 90475-32-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-Azetidinone, 4-(4-chlorophenyl)-1-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinone, 4-(4-chlorophenyl)-1-(4-methoxyphenyl)-(90475-32-4)
• EPA Substance Registry System: 2-Azetidinone, 4-(4-chlorophenyl)-1-(4-methoxyphenyl)-(90475-32-4)

Safety Data

• Hazardous Substances Data: 90475-32-4(Hazardous Substances Data)

Upstream product

• 105-36-2 ethyl bromoacetate 
• 1749-03-7 N-(4-chlorobenzylidene)-4-methoxyaniline 

Relevant articles and documents

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.

β-Lactam Formation by Ultrasound-promoted Reformatsky Type Reaction

Ultrasound was found to promote the reaction between ethyl bromoacetate, zinc, and a Schiff base such that an excellent yield of β-lactams was obtained in a few hours at room temperature.