Ethyl bromoacetate → N-[3-(4-tert-Butylcyclohexan-1-yl)phenyl]-4-ethoxycarbonylmethyloxy-3-methoxyphenylacetamide

HRID 7074

반응식

HRID 7074 반응식
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:29])[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([O:27][CH3:28])[CH:21]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:29])[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:22]([O:27][CH3:28])[CH:21]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 22019581N-[3-(4-tert-Butylcyclohexan-1-yl)phenyl]-4-hydroxy-3-methoxyphenylacetamide

생성물 1

HCID 22019615N-[3-(4-tert-Butylcyclohexan-1-yl)phenyl]-4-ethoxycarbonylmethyloxy-3-methoxyphenylacetamide수율 75.8%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-4-hydroxy-3-methoxyphenylacetamide (130 mg) and ethyl bromoacetate (84 mg) are dissolved in acetone, and thereto is added potassium carbonate (180 mg), and the reaction solution is heated under reflux for 18 hours. The reaction solution is filtered, and the filtrate is concentrated. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-4-ethoxycarbonylmethyloxy 3-methoxyphenylacetamide (120 mg). This product is dissolved in methanol (2 ml), and thereto is added 2 M aqueous sodium hydroxide solution (1 ml), and the mixture is stirred at 25° C. for 1 hour. The mixture is neutralized with acetic acid, and water is added thereto. The mixture is extracted with chloroform, and the organic layer is dried over sodium sulfate. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent: gradient from 0% to 25% chloroform/methanol) to give the desired compound (45 mg).

후처리

  1. temperaturethe reaction solution is heated
  2. temperatureunder reflux for 18 hours
  3. filtrationThe reaction solution is filtered
  4. concentrationthe filtrate is concentrated
  5. customThe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-c144e12b7636471bb89c322c897a8c5d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084176B2

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