N-(1-ethyl-1H-pyrazol-3-yl)-3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(phenylmethyl)oxy]benzamide → N-(1-Ethyl-1H-pyrazol-3-yl)-3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}benzamide
Reaction equation
[CH2:1]([N:3]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:30])[C:10]2[CH:15]=[C:14]([O:16]CC3C=CC=CC=3)[CH:13]=[C:12]([O:24][C@@H:25]([CH3:29])[CH2:26][O:27][CH3:28])[CH:11]=2)=[N:4]1)[CH3:2]>[Pd].C1COCC1.C(O)C>[CH2:1]([N:3]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:30])[C:10]2[CH:11]=[C:12]([O:24][C@@H:25]([CH3:29])[CH2:26][O:27][CH3:28])[CH:13]=[C:14]([OH:16])[CH:15]=2)=[N:4]1)[CH3:2]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
10% Palladium on carbon (1.9 g, 50% wet) was added under argon to N-(1-ethyl-1H-pyrazol-3-yl)-3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(phenylmethyl)oxy]benzamide (19.1 g, 46.7 mmol) in dry THF (100 mL) and ethanol (100 mL). The reaction mixture was degassed, placed under a hydrogen balloon and stirred for 16 hours. The mixture was filtered through diatomaceous earth and the filtrate was evaporated to give a brown oil. The residue was purified by column chromatography on silica, eluting with 40-65% ethyl acetate in hexanes, to give the desired product as a clear oil which crystallised on standing (11.35 g).
Workup
- customThe reaction mixture was degassed
- filtrationThe mixture was filtered through diatomaceous earth
- customthe filtrate was evaporated
- customto give a brown oil
- customThe residue was purified by column chromatography on silica
- washeluting with 40-65% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-930c9a28ee1a48dfaac5dbc926d9c136
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842694B2
Reaction notes
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