Synonyms:82290-86-6;2-Azetidinone, 4-(acetyloxy)-3-ethyl-;4-acetoxy-3-ethylazetidine-2-one;SCHEMBL8745355;3-ethyl-4-acetoxyazetidin-2-one;4-acetoxy-3-ethylazetidin-2-one;DTXSID70472619;VHOMYEKCMUWHJI-UHFFFAOYSA-N;FT-0732046
85.0-99.8% *data from raw suppliers
The study presents a practical stereoselective synthesis of 4-acetoxy-3-ethylazetidin-2-one, a key intermediate for the carbapenem antibiotic (+)-PS-5, using a Reformatsky reaction between methyl-a-bromo butyrate and N-4-methoxyp henyl-a-methylcin namylideneamine. The authors explored different conditions and reagents, finding that using toluene instead of benzene increased the yield and stereoselectivity of the reaction. The synthesized intermediate was then subjected to ozonolysis and Baeyer-Villiger oxidation to introduce the required 4-acetoxy group. The final step involved removing the N-aryl substituent using cerium(iv) ammonium nitrate (CAN) to obtain the desired product. The study also demonstrated the versatility of this method by synthesizing other functionalized β-lactams, highlighting the potential for creating a wide range of 3-alkyl side chain β-lactams using readily available and inexpensive starting materials.
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