Efficient synthesis of an enantiopure beta-lactam as an advanced precursor of thrombin and tryptase inhibitors.
A new and efficient synthesis of a beta-lactam that is an advanced precursor of inhibitors of thrombin and tryptase is reported. The reaction sequence is based on the use of an inexpensive enantiomerically pure starting material and is designed to allow access to both enantiomers of the target molecules by epimerization of a side-product obtained along the synthesis. An improved procedure for the epimerization step that takes advantage of the use of a polymer-supported and recyclable phase-transfer catalyst is described.
Annunziata
Rita
R
Dipartimento di Chimica Organica e Industriale and CNR-ISTM, Universita' degli Studi di Milano, Via Golgi 19 - 20133 Milano, Italy maurizio.benaglia@unimi.it
Benaglia
Maurizio
M
Cinquini
Mauro
M
Cozzi
Franco
F
Maggioni
Francesco
F
Puglisi
Alessandra
A
D000991:Antithrombins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015195:Drug Design; D007202:Indicators and Reagents; D008958:Models, Molecular; D015394:Molecular Structure; D012697:Serine Endopeptidases; D015842:Serine Proteinase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D053802:Tryptases; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000991:Antithrombins; D007202:Indicators and Reagents; D015842:Serine Proteinase Inhibitors; D047090:beta-Lactams; D012697:Serine Endopeptidases; D053802:Tryptases