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Imidazole → (2S)-2-[3-(2-Hydroxyethyl)-3-isoamylureido]-N-methyl-3-phenylpropionamide

HRID 2297720
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HRID 2297720 반응식
Cl.[CH3:2][NH:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].[C:15](N1C=CN=C1)(N1C=CN=C1)=[O:16].N1C=CN=C1.[OH:32][CH2:33][CH2:34][NH:35][CH2:36][CH2:37][CH:38]([CH3:40])[CH3:39]>O1CCCC1>[OH:32][CH2:33][CH2:34][N:35]([CH2:36][CH2:37][CH:38]([CH3:40])[CH3:39])[C:15](=[O:16])[NH:6][C@@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4]([NH:3][CH3:2])=[O:14]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 2784772-((3-Methylbutyl)amino)ethan-1-olHCID 13689669HCID 13689669, 화합물

생성물 1

HCID 59923466(2S)-2-[3-(2-Hydroxyethyl)-3-isoamylureido]-N-methyl-3-phenylpropionamide수율 93%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

In anhydrous tetrahydrofuran (7 ml) are suspended N-methyl-L-phenylalanine amide hydrochloride (Reference compound No. 8-2, 429 mg), 1,1′-carbonyldiimidazole (422 mg) and imidazole (136 mg) under a nitrogen atmosphere, and the suspension is stirred at room temperature for 20 minutes. A solution of N-(2-hydroxyethyl)isoamylamine (Reference compound No. 13-2, 525 mg) in anhydrous tetrahydrofuran (3 ml) is added to the reaction mixture, and the mixture is refluxed for 0.5 hour. The reaction mixture is concentrated under reduced pressure, a 10% aqueous citric acid solution is added to the concentrate, and the whole is extracted with ethyl acetate. The organic layer is washed with a 10% aqueous citric acid solution, water and saturated brine successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting oily matter is purified by silica gel column chromatography to give 626 mg (93%) of the titled compound (Compound No. 20-1).

후처리

  1. temperaturethe mixture is refluxed for 0.5 hour
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. additiona 10% aqueous citric acid solution is added to the concentrate
  4. extractionthe whole is extracted with ethyl acetate
  5. washThe organic layer is washed with a 10% aqueous citric acid solution, water and saturated brine successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting oily matter is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-984c0863294b48eea9e93259aa72568f
출처 데이터셋
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06492370B1

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