N-{(S)-1-hydroxy-3-phenyl-2-propyl}-5-benzyloxy-2-hydroxybenzamide → N-{(S)-1-hydroxy-3-phenyl-2-propyl}-2,5-dihydroxybenzamide
Reaction equation
[OH:1][CH2:2][C@@H:3]([NH:11][C:12](=[O:28])[C:13]1[CH:18]=[C:17]([O:19]CC2C=CC=CC=2)[CH:16]=[CH:15][C:14]=1[OH:27])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CO>[OH:1][CH2:2][C@@H:3]([NH:11][C:12](=[O:28])[C:13]1[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:14]=1[OH:27])[CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
In a flask equipped with a magnetic stirring bar and a rubber septum is dissolved the N-{(S)-1-hydroxy-3-phenyl-2-propyl}-5-benzyloxy-2-hydroxybenzamide in methanol. Nitrogen is bubbled through the solution and 10% Pd on charcoal is added. After flushing with nitrogen, the suspension is placed under hydrogen atmosphere and stirred for 2 hours. The suspension is flushed with nitrogen and filtered and rinsed over Celite. The filtrate is concentrated under vacuum. In this fashion is obtained N-{(S)-1-hydroxy-3-phenyl-2-propyl}-2,5-dihydroxybenzamide (85%).