131533-52-3

Upstream product

• 124156-34-9 1-p-anisyl-3-isopropylidene-4-carbomethoxy-2-azetidinone 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 131533-51-2 3-Isopropyl-1-(4-methoxy-phenyl)-4-oxo-3-phenylsulfanyl-azetidine-2-carboxylic acid methyl ester 
• 124156-20-3 (4-methoxyphenyl-benzylidene)-carbamic acid methyl ester 
• 124175-15-1 cis-1-p-anisyl-3-(1'-methylvinyl)-4-carbomethoxy-2-azetidinone 

Downstream Products

• 131533-53-4 Chloro-acetic acid 3-isopropylidene-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-ylmethyl ester 
• 131533-54-5 Chloro-acetic acid 1-(4-methoxy-phenyl)-3,4-dioxo-azetidin-2-ylmethyl ester 
• 131533-55-6 [2-(2-Chloro-acetoxymethyl)-1-(4-methoxy-phenyl)-4-oxo-azetidin-(3E)-ylidene]-acetic acid methyl ester 

Relevant academic research and scientific papers

Transformation of 4-acetoxy-3-vinylazetidin-2-ones to 3-(1-hydroxyethyl)azetidin-2-ones and 3-ethylideneazetidin-2-ones intermediates for carbapenem antibiotics

4-acetoxy-3-vinylazetidin-2-one and 4-acetoxy-3-isopropenylazetidin-2-one were transformed to the carbapenem intermediates 4-acethoxy-3-(1-hydroxyethyl)azetidin-2-ones and 4-acethoxy-3-[2-(2-hydroxypropyl)]-4-acetoxyazetidin-2-ones respectively by a sequence of direct bromohydrin formation followed by reductive debromination. Transformation of 4-formyl-3-vinylazetidin-2-ones to 4-acetoxy-3-ethylideneazetidin-2-ones was also carried out. We have also demonstrated the synthesis of a 6-vinylcarbapenem.

Addition of α-bromoesters to Azetidine-2,3-diones Promoted by Zinc-Trimethylchlorosilane: A General Synthesis of 3-trimethylsilyloxyazetidin-2-ones and α-Alkylidene β-lactams.

A convenient procedure for the preparation of α-alkylidene β-lactams from monocyclic azetidine-2,3-diones by means of the Reformatsky reaction is described.