3-[(1S)-2-methoxy-(1-methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide → 3-hydroxy-5-{[(2S)-1-methoxypropan-2-yl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide
Reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]([O:6][C:7]1[CH:8]=[C:9]([CH:19]=[C:20]([O:22]CC2C=CC=CC=2)[CH:21]=1)[C:10]([NH:12][C:13]1[CH:17]=[CH:16][N:15]([CH3:18])[N:14]=1)=[O:11])[CH3:5]>C1COCC1.CO.[Pd]>[OH:22][C:20]1[CH:19]=[C:9]([CH:8]=[C:7]([O:6][C@@H:4]([CH3:5])[CH2:3][O:2][CH3:1])[CH:21]=1)[C:10]([NH:12][C:13]1[CH:17]=[CH:16][N:15]([CH3:18])[N:14]=1)=[O:11]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 3-[(1S)-2-methoxy-(1-methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide (7.07 g) in THF (50 mL) and methanol (50 mL) was added 10% palladium on carbon (727 mg) as a slurry in THF (1 mL) and methanol (1 mL). The mixture was placed under vacuum and stirred under an atmosphere of hydrogen for 70 hours. The mixture was filtered through diatomaceous earth, and the diatomaceous earth washed with methanol (2×100 mL), followed by evaporation in vacuo. The residues were dissolved in ethyl acetate (10 mL), treated with isohexane (40 mL), the solid filtered off and washed with isohexane (50 mL) to afford the desired compound (5.17 g) which was used without further purification.
Workup
- filtrationThe mixture was filtered through diatomaceous earth
- washthe diatomaceous earth washed with methanol (2×100 mL)
- customfollowed by evaporation in vacuo
- dissolutionThe residues were dissolved in ethyl acetate (10 mL)
- additiontreated with isohexane (40 mL)
- filtrationthe solid filtered off
- washwashed with isohexane (50 mL)
Sources & evidence
- ORD record
- ord-9efcb57055aa477d955f96b65bd32096
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842694B2
Reaction notes
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