Réaction #586113

ord-6d2b561264f547138e77122e85f497ac

Équation de réaction

O=C(N[C@H](CO)Cc1ccccc1)c1cc(OCc2ccccc2)ccc1O
N-{(S)-1-hydroxy-3-phenyl-2-propyl}-5-benzyloxy-2-hydroxybenzamide
O=C(N[C@H](CO)Cc1ccccc1)c1cc(O)ccc1O
N-{(S)-1-hydroxy-3-phenyl-2-propyl }-2,5-dihydroxybenzamide
Rendement 85.0%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreIn a flask equipped with a magnetic stirring bar
  2. 2
    AutreNitrogen is bubbled through the solution and 10% Pd on charcoal
  3. 3
    workup.ADDITIONis added
  4. 4
    AutreAfter flushing with nitrogen
  5. 5
    AutreThe suspension is flushed with nitrogen
  6. 6
    Filtrationfiltered
  7. 7
    Lavagerinsed over Celite
  8. 8
    ConcentrationThe filtrate is concentrated under vacuum

Mode opératoire

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%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07767646B2uspto-grants-2010_08