322398-76-5

Upstream product

• 501-53-1 benzyl chloroformate 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 124-63-0 methanesulfonyl chloride 
• 72289-52-2 (2S,4R)-4-hydroxy-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid tert-butyl ester 

Downstream Products

• 1321614-40-7 N-[(1S)-1-carboxy-3-phenylpropyl]-L-alanyl-(4S)-4-{[(3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]amino}-L-proline 
• 1321614-47-4 tert-butyl N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanyl-(4S)-4-{[(3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoyl]amino}-L-prolinate 
• 1321614-37-2 tert-butyl (4S)-1-[(2S)-3-(acetylsulfanyl)-2-methylpropanoyl]-4-{[(3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoyl]amino}-L-prolinate 
• 1321614-27-0 tert-butyl (4S)-4-{[(3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoyl]amino}-L-prolinate 
• 1321614-28-1 1-benzyl 2-tert-butyl (2S,4S)-4-{[(3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoyl]amino}pyrrolidine-1,2-dicarboxylate 
• 1321615-14-8 tert-butyl N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-L-alanyl-(4S)-4-{[(3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoyl]amino}-L-prolinate 
• 1321615-13-7 tert-butyl (4S)-1-((2R)-bromopropanoyl)-4-{[(3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoyl]amino}-L-prolinate 
• 322398-80-1 N-benzyloxycarbonyl-4-cis-amino-L-proline tert-butyl ester 
• 322398-78-7 N-benzyloxycarbonyl-4-cis-azido-L-proline tert-butyl ester 

Relevant academic research and scientific papers

PROLINE DERIVATIVES FOR USE IN THE TREATMENT OF DIABETES

The present invention provides novel heterocyclic compounds and methods of preparing such compounds. The compounds of the invention are useful for palliative, curative or prophylactic treatment of diseases or conditions of diabetes and/or hypertension. This invention also relates to pharmaceutical compositions containing the compounds of the present invention, and methods for palliative, curative or prophylactic treatment of diseases or conditions of diabetes and/or hypertension. The present invention also provides pharmaceutical compositions consisting of the heterocyclic compounds along with one or more dyslipidemic agents, antiobesity agents, anti-hyperglycemic agents, antihypertensive agents and anti-inflammatory agents.

The synthesis of isomeric 4-prolinylamines and 4,4′-diprolinylamines

Starting from the previously described tert-butyl esters of 4-epimeric N-benzyloxycarbonyl-4-hydroxyprolines and N-benzyloxycarbonyl-4-trans- and 4-cis-trifluoroacetaminoproline tert-butyl esters, the corresponding unprotected 4-aminoprolines and a number of their partially protected derivatives were synthesized via the intermediate 4-O-mesyl and 4-azide derivatives. The reductive animation of N-benzyloxycarbonyl-4-oxoproline tert-butyl ester with ammonium acetate led to N-benzyloxycarbonyl-4-cis-4′-cis- and 4-cis-4′-trans-diprolinylamines. The 1H NMR and CD spectra of the synthesized compounds are described.