Reaction equation
[CH3:1][C:2]([Si:5]([CH3:35])([CH3:34])[O:6][CH2:7][C@@H:8]([O:10][C:11]1[CH:12]=[C:13]([CH:23]=[C:24]([O:26]CC2C=CC=CC=2)[CH:25]=1)[C:14]([NH:16][C:17]1[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=1)=[O:15])[CH3:9])([CH3:4])[CH3:3]>CO>[CH3:1][C:2]([Si:5]([CH3:35])([CH3:34])[O:6][CH2:7][C@@H:8]([O:10][C:11]1[CH:12]=[C:13]([CH:23]=[C:24]([OH:26])[CH:25]=1)[C:14]([NH:16][C:17]1[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=1)=[O:15])[CH3:9])([CH3:3])[CH3:4]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
3-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide (1.8 g, 3.64 mmol) was dissolved in methanol (50 mL) and the flask evacuated and purged with nitrogen (3 times). 10% Palladium on carbon (0.2 g) was added and the flask further evacuated and finally purged with hydrogen gas. The reaction mixture was stirred at ambient temperature for 16 hours until completion. The reaction mixture was evacuated and purged with nitrogen (3 times). The catalyst was filtered off, and the filtrate concentrated in vacuo to give the desired compound (1.45 g). 1H NMR δ (d6-DMSO): 0.02 (d, 6H), 0.83 (s, 9H), 1.18 (d, 3H), 3.66 (m, 2H), 3.72 (s, 3H), 4.51 (m, 1H), 6.42 (m, 1H), 6.52 (m, 1H), 6.90 (s, 1H), 7.02 (s, 1H), 7.55 (m, 1H), 9.58 (br s, 1H), 10.59 (br s, 1H). m/z 406 (M+H)+
Workup
- customthe flask evacuated
- custompurged with nitrogen (3 times)
- addition10% Palladium on carbon (0.2 g) was added
- customthe flask further evacuated
- customfinally purged with hydrogen gas
- customThe reaction mixture was evacuated
- custompurged with nitrogen (3 times)
- filtrationThe catalyst was filtered off
- concentrationthe filtrate concentrated in vacuo
Sources & evidence
- ORD record
- ord-2759f101f15344c89afc94811076524a
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977328B2
Linked notes
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