(5R,9R)-5-(tert-butoxycarbonyl)-1-(9H-fluoren-9-yl)-3-oxo-2,11-dioxa-7-thia-4-azatricosan-9-yl dodecanoate → (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(((R)-2-(dodecanoyloxy)-3-(dodecyloxy)propyl)thio)propanoic acid

Participants

Reaction Steps

A solution of ((5R,9R)-5-(tert-butoxycarbonyl)-1-(9H-fluoren-9-yl)-3-oxo-2,11-dioxa-7-thia-4-azatricosan-9-yl dodecanoate in 40% TFA in DCM (0.3 M) was stirred at room temperature until complete deprotection of tert-butyl group (2 hours). The reaction mixture was diluted in MTBE, washed three times with 1M citric acid (adjusted to pH3), and once with 1:2 1N HCl/brine. The organic layer was dried over anhydrous Na2SO4 and concentrated en vaccuo. The resulting waxy solid was used without further purification.

Provenance & Evidence