(S)-benzyl 4-(2-(1H-1,2,4-triazol-1-yl)acetamido)-5-(4-(4-fluorophenoxy)phenylamino)-5-oxopentylcarbamate → (S)-2-(2-(1H-1,2,4-triazol-1-yl)acetamido)-5-amino-N-(4-(4-fluorophenoxy)phenyl)pentanamide

Participants

Reaction Steps

Step (a) A flask was charged with (S)-benzyl 4-(2-(1H-1,2,4-triazol-1-yl)acetamido)-5-(4-(4-fluorophenoxy)phenylamino)-5-oxopentylcarbamate (700 mg, 1.25 mmol), prepared as in Example 1, palladium on carbon (10%, 70 mg) and methanol (30 mL) and the mixture was placed under a hydrogen atmosphere (balloon). The mixture was stirred 16 hours at ambient temperature and then concentrated and filtered. Product was purified from the residue by reverse phase HPLC to give (S)-2-(2-(1H-1,2,4-triazol-1-yl)acetamido)-5-amino-N-(4-(4-fluorophenoxy)phenyl)pentanamide (420 mg, 0.985 mmol, 79%) as an off-white solid.

Provenance & Evidence