65390-70-7

Upstream product

• 380869-78-3 3-Oxo-4-[(2R,3R)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-2-ylsulfanyl]-butyric acid ethyl ester 
• 61534-76-7 (3R,4R)-4-mercapto-3-phenoxyacetamidoazetidin-2-one 
• 35500-75-5 (1R)-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-7-one 
• 107-19-7 propargyl alcohol 
• 380869-81-8 2-Diazo-3-oxo-4-[(2R,3R)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-2-ylsulfanyl]-butyric acid ethyl ester 

Relevant academic research and scientific papers

Generation, electrocyclic ring opening, and unprecedented conversion of a 3-acylaminoazetinone into cis-3,4-disubstituted azetidinones

An attempt to synthesize the nucleus of cefaclor by insertion of an appropriately functionalized rhodium carbene into a β-lactam N-H bond leads instead to attack at sulfur, followed by fragmentation into a four-membered thietanone and a four-membered 3-acylaminoazetinone. The azetinone undergoes electrocyclic ring opening, with a calculated half-life of 11 s at 40°C, to a trans-disubstituted vinyl isocyanate, but can be trapped by saturated, unsaturated allylic and benzylic alcohols to form 3,4-disubstituted azetidinones in which the cis- isomer predominates.