80542-82-1

Basic information

• Product Name: cis-3-benzyloxycarbonylamino-4-methylazetidin-2-one
• CAS NO: 80542-82-1
• Molecular Weight: 234.255
• Mol File: 80542-82-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: cis-3-benzyloxycarbonylamino-4-methylazetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: cis-3-benzyloxycarbonylamino-4-methylazetidin-2-one(80542-82-1)
• EPA Substance Registry System: cis-3-benzyloxycarbonylamino-4-methylazetidin-2-one(80542-82-1)

Safety Data

• Hazardous Substances Data: 80542-82-1(Hazardous Substances Data)

Upstream product

• 112026-40-1 cis-3-benzyloxycarbonylamino-N-(4-methoxyphenyl)-4-methylazetidin-2-one 
• 93591-09-4 STABASE 
• 501-53-1 benzyl chloroformate 
• 112026-39-8 ethyl 3-(p-anisidino)-2-(benzyloxycarbonylamino)butanoate 
• 112026-38-7 ethyl (p-anisidino)-2-(benzoyloxycarbonylamino)but-2-enoate 
• 112026-37-6 ethyl 2-(benzyloxycarbonylamino)acetoacetate 

Downstream Products

• 80082-62-8 (2R,3S)-3-Benzyloxycarbonylamino-2-methyl-4-oxo-azetidine-1-sulfonatetetrabutyl-ammonium; 

Relevant articles and documents

Stereoselective synthesis of cis-4-(substituted) monobactams from ethyl acetoacetate

The stereoselective synthesis of cis-3-amino-4-methyl-2-oxoazetidine-1-sulphonic acid (25) from ethyl acetoacetate is described. Nitrosation of this compound and reduction of the resulting oxime gave the corresponding amine, which after treatment with different acyl halides, yielded the acylamino derivatives (6)-(8). Condensation with p-anisidine gave the enamines (12)-(14), which were then reduced to the β-amino acid esters (15)-(17). Stereoselective cyclization with Grignard reagents as base, and appropriate deprotection and sulphonation of the resulting β-lactams (18)-(20), led to the title compounds.