methyl 3-(4-{[4-{{2-[(benzhydryloxy)carbonyl]phenyl}[(benzyloxy)(oxo)acetyl]amino}-N-(methoxycarbonyl)-L-phenylalanyl]amino}butoxy)-1-hydroxy-2-naphthoate → methyl 3-(4-{[4-[(carboxycarbonyl)(2-carboxyphenyl)amino]-N-(methoxycarbonyl)-L-phenylalanyl]amino}butoxy)-1-hydroxy-2-naphthoate

Participants

Reaction Steps

To methyl 3-(4-{[4-{{2-[(benzhydryloxy)carbonyl]phenyl}[(benzyloxy)(oxo)acetyl]amino}-N-(methoxycarbonyl)-L-phenylalanyl]amino}butoxy)-1-hydroxy-2-naphthoate (32 mg, 0.033 mmol) in dioxane (1 mL) under N2 was added 10% Pd—C (5 mg) followed by 60% HClO4 (1 drop). The reaction was stirred under 1 atmosphere of H2 for 4 hours and filtered. The solution was applied to a reverse phase HPLC column and purified by eluting with 0% to 70% gradient of acetonitrile/0.1% aqueous trifluoroacetic acid to provide the titled compound (13 mg, 56%).

Provenance & Evidence