Improved scalable syntheses of mono- and bis-urethane derivatives of ornithine.
In the search for a practical route to ornithine bisurethane derivatives useful for peptide synthesis, we elaborated the simple and efficient (86% yield) synthesis of N(epsilon)-tert-butoxycarbonyl-L-ornithine copper(II) complex (1). This served as substrate for obtaining N(epsilon)-tert-butoxycarbonyl-L-ornithine (2), N(alpha)-benzyloxycarbonyl-N(epsilon)-tert-butoxycarbonyl-L-ornithine (3) and N(alpha)-(9-fluorenyl)methoxycarbonyl-N(epsilon)-tert-butoxycarbonyl-L-ornithine (4). These were synthesized in 94-95% yields and with a purity above 99%.
Wiejak
S
S
Laboratory of Chemistry, Technical University of Opole, Poland.
Masiukiewicz
E
E
Rzeszotarsk
B
B
D002152:Calorimetry, Differential Scanning; D002851:Chromatography, High Pressure Liquid; D003300:Copper; D007202:Indicators and Reagents; D009952:Ornithine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D014520:Urethane / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D007202:Indicators and Reagents; D014520:Urethane; D003300:Copper; D009952:Ornithine