Ethyl Acetate → N-(2-t-Butyl-5-carboxyphenyl)-3-(4-acetyl-2-methoxyphenyl)octanamide

HRID 1418225노트

반응식

HRID 1418225 반응식
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]

참가 물질

7

반응물 3

HCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 19348677N-(2-t-butyl-5-methoxycarbonylphenyl)-3-[4-(1-hydroxyethyl)-2-methoxyphenyl)-octanamide

생성물 1

HCID 19348740N-(2-t-Butyl-5-carboxyphenyl)-3-(4-acetyl-2-methoxyphenyl)octanamide수율 101.2%

시약·촉매·용매 3

HCID 178419074HCID 178419074, 화합물촉매HCID 6344Dichloromethane용매HCID 8058Hexane용매2회

실험 절차

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.

후처리

  1. stirringThe reaction mixture was stirred at room temperature for 1 hour

출처 및 근거

ORD 기록
ord-55ad22bff8fd4a54867adeed39e8b150
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05880147

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