18087-65-5

Upstream product

• 103301-78-6 1-benzyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 

Downstream Products

• 18087-66-6 1-Benzyl-4,5-dichlor-1H-pyrrol-2-carbonsaeure 
• 100-51-6 benzyl alcohol 
• 106116-09-0 L-5-Oxo-1-(trimethylsilyl)prolin-benzylester 
• 94885-52-6 benzyl (L)-pyroglutamate 
• 106116-10-3 L-1-Benzhydryl-5-oxoprolin-benzylester 

Relevant academic research and scientific papers

Amino Acids, 9 - Reactions of 5-Oxoproline Derivatives with Phosphorus Pentachloride - Synthesis of Chloro-pyrrole-2-carboxylic Acid Derivatives

N-Benzyl-4,5-dichloro-1H-pyrrole-2-carboxylic esters 6 are formed from N-benzyl-5-oxoproline esters 5 and PCl5 via differently chlorinated intermediates.The N-benzhydryl- L-3 and N-acyl-5-oxoproline esters L-4, on the other hand, suffer cleavage of the N-substituent in the course of this reaction sequence to give L-4,4,5-trichloro-3,4-dihydro-2H-pyrrole-2-carboxylic esters 18, which are dehydrohalogenated in the presence of base, yielding 4,5-dichloro-1H-pyrrole-2-carboxylic esters 20.These reactions provide the best access to 4,5-dichloro-1H-pyrrole-2-carboxylic acid derivatives which, in turn, can serve as precursors in the synthesis of pyoluteorin type compounds.

Amino Acids, 10. - Reactions of 5-Oxoproline Derivatives with Thionyl and Oxalyl Chloride

Reactions of N-methyl- and N-benzyl-substituted 5-oxoproline methylesters (1a,b) with thionyl or oxalyl chloride yield N-substituted 5-chloro-2,3-dihydro-1H-pyrrole-2-carboxylic esters.These esters, as α-chloro enamines, undergo further electrophilic reac