3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)-5-[(phenylmethyl)oxy]benzamide → (S)-3-hydroxy-5-(1-methoxypropan-2-yloxy)-N-(5-methylpyrazin-2-yl)benzamide
Reaction equation
[CH3:1][C@H:2]([O:6][C:7]1[CH:8]=[C:9]([CH:20]=[C:21]([O:23]CC2C=CC=CC=2)[CH:22]=1)[C:10]([NH:12][C:13]1[CH:18]=[N:17][C:16]([CH3:19])=[CH:15][N:14]=1)=[O:11])[CH2:3][O:4][CH3:5]>C(O)C>[OH:23][C:21]1[CH:20]=[C:9]([CH:8]=[C:7]([O:6][C@@H:2]([CH3:1])[CH2:3][O:4][CH3:5])[CH:22]=1)[C:10]([NH:12][C:13]1[CH:18]=[N:17][C:16]([CH3:19])=[CH:15][N:14]=1)=[O:11]Participants
3
Procedure
3-{[(1S)-1-Methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)-5-[(phenylmethyl)oxy]benzamide (4.5 g, 11 mmol) was dissolved in ethanol (35 mL) and THF (35 mL) and the flask evacuated and purged with argon (3 times). 10% Palladium on carbon (0.45 g) was added and the flask further evacuated and finally purged with hydrogen gas. The reaction mixture was stirred at ambient temperature for 20 hours until completion. The reaction mixture was evacuated and purged with nitrogen (3 times). The catalyst was filtered off through celite, and the filtrate concentrated in vacuo to give the desired compound (3.21 g).
Workup
- customTHF (35 mL) and the flask evacuated
- custompurged with argon (3 times)
- addition10% Palladium on carbon (0.45 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 through celite
- concentrationthe filtrate concentrated in vacuo
Sources & evidence
- ORD record
- ord-f459c7b02e984674aa3d5eb055213174
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745475B2
Reaction notes
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