N-{(S)-1-hydroxy-3-phenyl-2-propyl}-5-benzyloxy-2-hydroxybenzamide → N-{(S)-1-hydroxy-3-phenyl-2-propyl}-2,5-dihydroxybenzamide

HRID 1243272Notes

Reaction equation

HRID 1243272 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]=1

Participants

3

Reactant 1

HCID 17751795N-{(S)-1-hydroxy-3-phenyl-2-propyl}-5-benzyloxy-2-hydroxybenzamide

Product 1

HCID 10469284N-{(S)-1-hydroxy-3-phenyl-2-propyl}-2,5-dihydroxybenzamideYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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%).

Workup

  1. customIn a flask equipped with a magnetic stirring bar
  2. customNitrogen is bubbled through the solution and 10% Pd on charcoal
  3. additionis added
  4. customAfter flushing with nitrogen
  5. customThe suspension is flushed with nitrogen
  6. filtrationfiltered
  7. washrinsed over Celite
  8. concentrationThe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-c985136e55be464b952aacd30c033b21
Source dataset
uspto-grants-2006_10
Patent number
US07119068B2

Reaction notes

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