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 548769Notes

Reaction equation

HRID 548769 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 96.2%

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).

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-4c1f2a21940747c4b94dcafe9ea99558
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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