Reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:28](=[O:35])[N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[CH2:10][C:11]1[CH:12]=[C:13]([C:17]#[C:18][CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:14]=[CH:15][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd+2]>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:28](=[O:35])[N:29]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1)[CH2:10][C:11]1[CH:12]=[C:13]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[O:22])[CH:14]=[CH:15][CH:16]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
tert-Butyl (S)-5-(3-(2-((tert-butoxycarbonyl)amino)-3-oxo-3-(piperidin-1-yl)propyl)phenyl)pent-4-ynoate (Compound SP430) (4.84 g, 9.99 mmol) was dissolved in ethyl acetate (40 ml), and 10% palladium(II) on carbon (968 mg) was added under a nitrogen atmosphere. The mixture was then stirred at room temperature for 3.5 hours under a hydrogen atmosphere. After filtration through celite, the filtrate was concentrated under reduced pressure to afford the title compound (Compound SP431) (4.74 g, 97%).
Workup
- filtrationAfter filtration through celite
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-dc1dbe1f4842407dbf520112eaf2ae8f
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409952B2
Linked notes
Loading…