322398-77-6

Upstream product

• 10387-40-3 potassium thioacetate 
• 147489-27-8 (2S)-4-oxo-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid tert-butyl ester 
• 124-63-0 methanesulfonyl chloride 
• 224321-05-5 (2S,4S)-4-hydroxy-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid tert-butyl ester 

Downstream Products

• 322398-83-4 N-benzyloxycarbonyl-4-trans-amino-L-proline tert-butyl ester 
• 322398-79-8 N-benzyloxycarbonyl-4-trans-azido-L-proline tert-butyl ester 

Relevant academic research and scientific papers

Pyrrolidine derivatives

The present invention relates to pyrrolidine derivatives and dimeric forms and/or pharmaceutically acceptable esters, and/or salts thereof. The compounds are useful as inhibitors of metalloproteases, e.g. zinc proteases, particularly zinc hydrolases, and which are effective in treating disease states are associated with vasoconstriction of increasing occurrences.

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.