tert-butyl 3-({3-(benzyloxy)-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate → tert-Butyl 3-({3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate

HRID 20550Notes

Reaction equation

HRID 20550 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:27]=[C:28]([O:30][C@@H:31]([CH3:35])[CH2:32][O:33][CH3:34])[CH:29]=1)[C:12]([NH:14][C:15]1[CH:19]=[CH:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[N:16]=1)=[O:13])C1C=CC=CC=1>C1COCC1.C(O)C>[OH:8][C:9]1[CH:10]=[C:11]([CH:27]=[C:28]([O:30][C@@H:31]([CH3:35])[CH2:32][O:33][CH3:34])[CH:29]=1)[C:12]([NH:14][C:15]1[CH:19]=[CH:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[N:16]=1)=[O:13]

Participants

4

Reactant 1

HCID 59127136tert-butyl 3-({3-(benzyloxy)-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate

Product 1

HCID 59127185tert-Butyl 3-({3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylateYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 3-({3-(benzyloxy)-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate (23 g, 47.8 mmol) in THF (140 mL) and ethanol (140 mL) was evacuated and purged with nitrogen (×3). 10% Palladium on carbon (2.3 g, 10% w/w) was added and reaction mixture was evacuated and finally purged with hydrogen gas. Reaction mixture was left to stir at ambient temperature under a hydrogen balloon for 16-hours. Pd/C was filtered through diatomaceous earth and the filtrate concentrated in vacuo to give a white, foam (18 g, 97%).

Workup

  1. custompurged with nitrogen (×3)
  2. addition10% Palladium on carbon (2.3 g, 10% w/w) was added
  3. customreaction mixture
  4. customwas evacuated
  5. customfinally purged with hydrogen gas
  6. customReaction mixture
  7. waitwas left
  8. filtrationPd/C was filtered through diatomaceous earth
  9. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-8bf7d6cee8114df88f7824bf2a2e6cf1
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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