tert-butyl 3-[(3-(benzyloxy)-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzoyl)amino]-1H-pyrazole-1-carboxylate → tert-butyl 3-[(3-hydroxy-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzoyl)amino]-1H-pyrazole-1-carboxylate

HRID 20586Notes

Reaction equation

HRID 20586 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:27]=[C:28]([O:30][C@@H:31]([CH3:44])[CH2:32][O:33][Si:34]([CH:41]([CH3:43])[CH3:42])([CH:38]([CH3:40])[CH3:39])[CH:35]([CH3:37])[CH3:36])[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]([CH3:44])[CH2:32][O:33][Si:34]([CH:41]([CH3:43])[CH3:42])([CH:35]([CH3:37])[CH3:36])[CH:38]([CH3:39])[CH3:40])[CH:29]=1)[C:12]([NH:14][C:15]1[CH:19]=[CH:18][N:17]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[N:16]=1)=[O:13]

Participants

3

Reactant 1

HCID 59346886tert-butyl 3-[(3-(benzyloxy)-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzoyl)amino]-1H-pyrazole-1-carboxylate

Product 1

HCID 59346873tert-butyl 3-[(3-hydroxy-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzoyl)amino]-1H-pyrazole-1-carboxylateYield 91.1%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of tert-butyl 3-[(3-(benzyloxy)-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzoyl)amino]-1H-pyrazole-1-carboxylate (90 mg, 0.144-mmol) in 1:1 mixture of THF/ethanol was evacuated and purged with nitrogen (×3). 10% Palladium on carbon was added and the reaction mixture was evacuated and purged with nitrogen and then evacuated and finally purged with hydrogen gas. The reaction mixture was left to stir at ambient temperature under an atmosphere of hydrogen for 6 hours. The Palladium catalyst was filtered through diatomaceous earth. The filtrate was evaporated to give a crude solid (70 mg)

Workup

  1. customwas evacuated
  2. custompurged with nitrogen (×3)
  3. addition10% Palladium on carbon was added
  4. customthe reaction mixture was evacuated
  5. custompurged with nitrogen
  6. customevacuated
  7. customfinally purged with hydrogen gas
  8. waitThe reaction mixture was left
  9. filtrationThe Palladium catalyst was filtered through diatomaceous earth
  10. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-e69d74f5ba3d450295d054083235e89a
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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