Solid-phase library synthesis of alkoxyprolines.
The library synthesis of alkoxyprolines was achieved using an acid-stable, nucleophile-cleavable solid support. A hydroxythiophenol linker derived from Merrifield resin was esterified with the corresponding ethers of BOC-hydroxyproline. Removal of the BOC protecting group with trifluoroacetic acid followed by acylation gave solid-supported hydroxyproline derivatives. Cleavage from the solid support with excess primary amines or excess secondary amines followed by purification of the crude products from the excess amine by supported liquid-liquid extraction gave the alkoxyproline library in high purity.
Boldi
A M
AM
ChemRx Advanced Technologies, Inc., A Discovery Partners International Company, 385 Oyster Point Boulevard, Suite 1, South San Francisco, California 94080, USA.
Dener
J M
JM
Hopkins
T P
TP
D000478:Alkylation; D020650:Combinatorial Chemistry Techniques; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D011392:Proline / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D011480:Protease Inhibitors / Q000138:chemical synthesis*; D013056:Spectrophotometry, Ultraviolet
D007202:Indicators and Reagents; D011480:Protease Inhibitors; D011392:Proline