Melatonin → HCID 15382325, 화합물

HRID 612522

반응식

HRID 612522 반응식
[CH3:1][C:2]([NH:4][CH2:5][CH2:6][C:7]1[C:11]2[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=2[NH:9][CH:8]=1)=[O:3].[H-].[Na+].[C:20](Cl)(=[O:22])[CH3:21].[O:24]1CC[CH2:26][CH2:25]1>>[C:20]([N:9]1[C:10]2[C:11](=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[C:7]([CH2:6][CH2:5][NH:4][C:2](=[O:3])[CH3:1])=[CH:8]1)(=[O:22])[CH3:21].[C:20]([N:9]1[C:10]2[C:11](=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[C:7]([CH2:6][CH2:5][N:4]([C:25]([CH3:26])=[O:24])[C:2](=[O:3])[CH3:1])=[CH:8]1)(=[O:22])[CH3:21]

참가 물질

6

반응물 4

HCID 896MelatoninHCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 24758Sodium hydride

생성물 2

HCID 15382325HCID 15382325, 화합물HCID 44359266N-[2-(1-acetyl-5-methoxyindol-3-yl)ethyl]diacetamide

실험 절차

Melatonin (126 mg) is dissolved in tetrahydrofuran (10 ml) in a 50 ml round-bottomed flask, sodium hydride (200 mg) is then added and the mixture is maintained at reflux (10 min). After cooling (0° C.), acetyl chloride is added and the mixture is kept stirring overnight (room temperature). After filtration and dilution (EtOAc), the organic phase is washed with water and then separated on a silica plate. N-[2-(1-Acetyl-5-methoxyindol-3-yl)ethyl]acetamide (1) is mainly obtained, along with a side product, N-[2-(1-acetyl-5-methoxyindol-3-yl)ethyl]diacetamide (10) (cf. Example 10).

후처리

  1. temperaturethe mixture is maintained
  2. temperatureat reflux (10 min)
  3. additionis added
  4. filtrationAfter filtration and dilution (EtOAc)
  5. washthe organic phase is washed with water
  6. customseparated on a silica plate

출처 및 근거

ORD 기록
ord-e8ffc787ee6e427eb29eefa7d99e3a33
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06004991

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