Ethyl Acetate → N-(2-t-Butyl-5-carboxyphenyl)-3-(4-acetyl-2-methoxyphenyl)octanamide
Reaction equation
C[N+]1([O-])CCOCC1.[C:9]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([O:21]C)=[O:20])=[CH:15][C:14]=1[NH:23][C:24](=[O:43])[CH2:25][CH:26]([C:32]1[CH:37]=[CH:36][C:35]([CH:38]([OH:40])[CH3:39])=[CH:34][C:33]=1[O:41][CH3:42])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])([CH3:12])([CH3:11])[CH3:10].C(OCC)(=O)C>C(Cl)Cl.CCCCCC.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:9]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][C:14]=1[NH:23][C:24](=[O:43])[CH2:25][CH:26]([C:32]1[CH:37]=[CH:36][C:35]([C:38](=[O:40])[CH3:39])=[CH:34][C:33]=1[O:41][CH3:42])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])([CH3:10])([CH3:11])[CH3:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
500 mg of 4A molecular sieves and 185 mg (1.58 mmol) of 4-methylmorpholin-4-oxide were added to a solution of 466 mg (0.964 mmol) of N-(2-t-butyl-5-methoxycarbonylphenyl)-3-[4-(1-hydroxyethyl)-2-methoxyphenyl)-octanamide [prepared as described in step (i) above] in 10 ml of methylene chloride, and the resulting mixture was stirred at room temperature for 10 minutes. At the end of this time, 34 mg (0.097 mmol) of tetrapropylammonium perruthenate were added to the mixture. The reaction mixture was stirred at room temperature for 1 hour, after which it was diluted with hexane and the diluted solution was subjected to column chromatography through 25 g of silica gel, using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent, to give 456 mg (yield 98%) of the title ketone derivative as a foam-like substance.
Workup
- stirringThe reaction mixture was stirred at room temperature for 1 hour
Sources & evidence
- ORD record
- ord-55ad22bff8fd4a54867adeed39e8b150
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05880147
Reaction notes
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