55686-17-4

Upstream product

• 5874-61-3 4-benzyl-2-phenyl-2-oxazolin-5-one 
• 105-39-5 chloroacetic acid ethyl ester 
• 436156-55-7 benzyl N-(2,4,6-trimethoxy)benzyl-N-chloroacetyl-L-phenylalaninate 
• 436156-49-9 benzyl N-(2,4-dimethoxy)benzyl-N-chloroacetyl-L-phenylalaninate 
• 436156-40-0 benzyl N-(2,4,6-trimethoxy)benzyl-L-phenylalaninate 
• 436156-36-4 benzyl N-(2,4-dimethoxy)benzyl-L-phenylalaninate 
• 2462-32-0 L-phenylalanine benzyl ester hydrochloride 
• 436156-71-7 4-benzyl-1-(2,4,6-trimethoxy)benzyl-4-benzyoxycarbonyl-2-azetidinone 
• 76-05-1 trifluoroacetic acid 
• 436156-67-1 4-benzyl-1-(2,4-dimethoxy)benzyl-4-benzyloxycarbonyl-2-azetidinone 

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.