tert-butyl(S)-4-(3-(isoquinolin-6-yl)isoxazol-5-yl)-1-phenylbut-3-yn-2-ylcarbamate → tert-Butyl(R)-4-(3-(isoquinolin-6-yl)isoxazol-5-yl)-1-phenylbutan-2-ylcarbamate
Reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:15]=[C:14]([C:16]#[C:17][C@@H:18]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[O:13][N:12]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1>CO.[Pd]>[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:15]=[C:14]([CH2:16][CH2:17][C@@H:18]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:30])[CH3:32])[CH2:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[O:13][N:12]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1Participants
4
Procedure
To a solution of tert-butyl(S)-4-(3-(isoquinolin-6-yl)isoxazol-5-yl)-1-phenylbut-3-yn-2-ylcarbamate (0.089 g, 0.20 mmol) in 10 mL of MeOH was added 10% palladium on carbon (0.089 g). Hydrogen was bubbled through the reaction mixture for 5 minutes. The reaction was kept under a balloon atmosphere of hydrogen for 2 hours. The reaction mixture was then filtered through Celite and concentrated under reduced pressure. The obtained tert-butyl(R)-4-(3-(isoquinolin-6-yl)isoxazol-5-yl)-1-phenylbutan-2-ylcarbamate was used without any purification.
Workup
- customHydrogen was bubbled through the reaction mixture for 5 minutes
- filtrationThe reaction mixture was then filtered through Celite
- concentrationconcentrated under reduced pressure
- customThe obtained tert-butyl(R)-4-(3-(isoquinolin-6-yl)isoxazol-5-yl)-1-phenylbutan-2-ylcarbamate was used without any purification
Sources & evidence
- ORD record
- ord-ab4a57fc0189499a8718bae3c2c48c77
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897619B2
Reaction notes
Loading…