50708-28-6

Basic information

• Product Name: 2-Azetidinone, 3-amino-4-(4-methoxyphenyl)-1-(4-methylphenyl)-, cis-
• CAS NO: 50708-28-6
• Molecular Formula: C17H18N2O2
• Molecular Weight: 282.342
• Mol File: 50708-28-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-Azetidinone, 3-amino-4-(4-methoxyphenyl)-1-(4-methylphenyl)-, cis-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinone, 3-amino-4-(4-methoxyphenyl)-1-(4-methylphenyl)-, cis-(50708-28-6)
• EPA Substance Registry System: 2-Azetidinone, 3-amino-4-(4-methoxyphenyl)-1-(4-methylphenyl)-, cis-(50708-28-6)

Safety Data

• Hazardous Substances Data: 50708-28-6(Hazardous Substances Data)

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 106-49-0 p-toluidine 
• 3246-78-4 N-(4-methoxybenzylidene)-4-methylaniline 
• 83306-66-5 N-(p-methoxybenzylidene)-p-toluidine 
• 77869-36-4 cis-1-(4'-methylphenyl)-3-(1'-methyl-2'-carbomethoxyvinylamino)-4-(4'-methoxyphenyl)-azetidin-2-one 
• 70208-19-4 (E)-3-[(2R,3S)-2-(4-Methoxy-phenyl)-4-oxo-1-p-tolyl-azetidin-3-ylamino]-but-2-enoic acid ethyl ester 

Downstream Products

• 50708-29-7 cis 1-p-tolyl-3-phenoxyacetamido-4-p-anisylazetidine 2-one 

Relevant articles and documents

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.

Some Novel Monocyclic cis-β-Lactams from Glycine

Enamine derivatives (Ia, b) obtained by the condensation of glycine and β-dicarbonyl compounds have been utilised for the stereoselective synthesis of cis-β-lactams.Addition of POCl3 to a mixture of the potassium salts (I), imines (IIa-c and III) and triethylamine gives 3-enamino-2-azetidinones (IV, VI, VII, X and XXI) in 30-40 percent yield.Imines (IId and IIe) prepared from ethyl glycinate hydrochloride and aromatic aldehydes, when subjected to this reaction yield 3-enamino-β-lactams (XIII and XVII) carrying an ester function.The protecting β-dicarbonyl function canbe easily removed with ethanol/HCl to generate the α-amino-β-lactams (V, VIII, XI, XIV, XVIII and XXII) which have been used as the progenitors for the preparation of 3-amido-2-azetidinones.The α-amido-β-lactams (XV and XIX) having an ester function on treatment with 0.1 N NaOH in acetone get converted into the novel α-amido-β-lactams (XVI and XX) carrying a free carboxy function essential for antibacterial activity.