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 1011739Notes

Reaction equation

HRID 1011739 reaction equation
[CH3:1][C@H:2]([O:6][C:7]1[CH:8]=[C:9]([C:21]([NH:23][C:24]2[CH:28]=[CH:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[N:25]=2)=[O:22])[CH:10]=[C:11]([O:13]CC2C=CC=CC=2)[CH:12]=1)[CH2:3][O:4][CH3:5]>C1COCC1.C(O)C>[OH:13][C:11]1[CH:10]=[C:9]([C:21]([NH:23][C:24]2[CH:28]=[CH:27][N:26]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[N:25]=2)=[O:22])[CH:8]=[C:7]([O:6][C@@H:2]([CH3:1])[CH2:3][O:4][CH3:5])[CH:12]=1

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 1,1-dimethylethyl 3-[({3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(phenylmethyl)oxy]phenyl}carbonyl)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. The reaction mixture was left to stir at RT under a hydrogen balloon for 16 hours. The palladium on carbon 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. waitThe reaction mixture was left
  7. filtrationThe palladium on carbon was filtered through diatomaceous earth
  8. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-76694017b96a4b86a6ddbb3c751d2191
Source dataset
uspto-grants-2011_07
Patent number
US07977328B2

Reaction notes

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