Reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24](/[CH:28]=[CH:29]/[C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[CH:31]=3)[CH:23]=2)=[O:20])=[CH:14][C:13]=1[O:37][CH3:38])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.C(O)(=O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[CH:31]=3)[CH:23]=2)=[O:20])=[CH:14][C:13]=1[O:37][CH3:38])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
4-[2-(tert-Butoxycarbonylamino)ethoxy]-3-methoxy-N-[3-[(E)-2-(3-methylphenyl)vinyl]phenyl]phenylacetamide (100 mg) is dissolved in methanol (10 ml) and acetic acid (1 ml), and thereto is added 10% palladium on carbon (10 mg), and the mixture is subjected to catalytic hydrogenation at 50° C. The catalyst is removed by filtration, and the solvent is evaporated to give 4-[2-(tert-butoxycarbonylamino)ethoxy]-3-methoxy-N-[3-[2-(3-methylphenyl)ethyl]phenyl]phenylacetamide (80 mg). This product is treated with 10% hydrogen chloride-methanol to give the desired compound (50 mg).
Workup
- customis subjected to catalytic hydrogenation at 50° C
- customThe catalyst is removed by filtration
- customthe solvent is evaporated
Sources & evidence
- ORD record
- ord-6faf8d70cb6a4ac0804d8ed31f4ed67f
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07084176B2
Linked notes
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