344765-04-4

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 2462-32-0 L-phenylalanine benzyl ester hydrochloride 

Downstream Products

• 344765-26-0 4-benzyl-1-(4-methoxy)benzyl-4-benzyloxycarbonyl-2-azetidinone 
• 344765-39-5 4-benzyl-1-(p-methoxybenzyl)-4-carboxy-2-azetidinone 
• 344765-13-5 benzyl N-(4-methoxy)benzyl-N-chloroacetyl-L-phenylalaninate 

Relevant academic research and scientific papers

Amino acid-derived 4-alkyl-4-carboxy-2-azetidinones. New insights into β-lactam ring formation and n-deprotection

The preparation and N-deprotection of a series of phenylalanine-derived 2-azetidinones incorporating 2,4-dimethoxybenzyl (Dmb), 2,3,4-, 2,4,6- and 3,4,5-trimethoxybenzyl (Tmb) groups at 1 position are described. The base-promoted cyclization of the corresponding methoxy-substituted Nαbenzyl-Nα-chloroacetyl derivatives to the 1,4,4-trisubstituted azetidinones proceeded with moderate to good yields, except for the 2,4,6-Tmb analogue. In spite of the number and position of the OMe groups, N-unsubstituted β-lactams were obtained by oxidative debenzylation using potassium peroxodisulfate. Alternatively, debenzylation of Pmb, Dmb and Tmb 2-azetidinones with TFA/anisole resulted in concomitant β-lactam opening to α-benzylaspartic acid derivatives.