Melatonin → HCID 15382325、化合物

HRID 370055

反応式

HRID 370055 の反応式
[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]

参加物

6

反応物 4

HCID 896MelatoninHCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 24758Sodium hydride

生成物 2

HCID 15382325HCID 15382325、化合物HCID 44359266N-[2-(1-acetyl-5-methoxyindol-3-yl)ethyl]diacetamide

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-707afcc28a634645995c8dc135c38eae
出典データセット
uspto-grants-2000_10
特許番号
US06140372

関連ノート

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