80082-64-0

Upstream product

• 112026-51-4 ethyl 3-(p-anisidino)-2-(phenylacetylamino)butanoate 
• 112026-50-3 ethyl 3-(p-anisidino)-2-(phenylacetylamino)but-2-enoate 
• 112026-52-5 cis-N-(4-methoxyphenyl)-4-methyl-3-(phenylacetylamino)azetidin-2-one 
• 92246-33-8 ethyl 2-(phenylacetylamino)acetoacetate 
• 32503-27-8 tetra(n-butyl)ammonium hydrogensulfate 
• 87791-64-8 cis-4-methyl-3-(phenylacetylamino)azetidin-2-one 
• 80082-52-6 Methanesulfonic acid (1R,2S)-2-carbamoyl-1-methyl-2-phenylacetylamino-ethyl ester 
• 80082-58-2 C₁₆H₃₆N⁽¹⁺⁾*C₁₃H₁₇N₂O₈S₂^(1-) 

Downstream Products

• 80082-65-1 (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid 
• 122553-92-8 cis-4-methyl-3-phenylacetylamino-2-oxoazetidine-1-sulphonic acid sodium salt 

Relevant academic research and scientific papers

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.

Monobactams. Stereospecific Synthesis of (S)-3-Amino-2-oxoazetidine-1-sulfonic Acids

A facile, stereospecific synthesis of 3-amino-2-oxoazetidine-1-sulfonic acids (monobactams) by the cyclization of acyl sulfamates derived from β-hydroxy amino acids is described.