Acetyl chloride → N-{3-[2,3-Dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-oxetan-3-ylmethyl}-acetamide

HRID 2171037노트

반응식

HRID 2171037 반응식
[NH2:1][CH2:2][C:3]1([CH2:7][O:8][C:9]2[C:14]([O:15][CH3:16])=[C:13]([O:17][CH3:18])[CH:12]=[CH:11][C:10]=2[C:19]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=2[CH2:21][CH2:22][C:23]3=[O:28])[CH2:6][O:5][CH2:4]1.C(N(CC)CC)C.[C:36](Cl)(=[O:38])[CH3:37]>ClCCl.O>[CH3:16][O:15][C:14]1[C:13]([O:17][CH3:18])=[CH:12][CH:11]=[C:10]([C:19]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=2[CH2:21][CH2:22][C:23]3=[O:28])[C:9]=1[O:8][CH2:7][C:3]1([CH2:2][NH:1][C:36](=[O:38])[CH3:37])[CH2:4][O:5][CH2:6]1

참가 물질

6

반응물 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 674679514-[2-(3-Aminomethyl-oxetan-3-ylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one2회

생성물 1

HCID 54577376N-{3-[2,3-Dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-oxetan-3-ylmethyl}-acetamide

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a stirring solution of 4-[2-(3-Aminomethyl-oxetan-3-ylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one (Compound 191) (150 mg, 0.391 mmol) in dichloromethane (15 mL), were added triethylamine (118 mg, 1.174 mmol) and acetyl chloride (61 mg, 0.777 mmol) and the resultant reaction mixture was stirred at RT for 16 h. The reaction mixture was diluted with water and extracted with dichloromethane (3×). The combined dichloromethane layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0-2% methanol in dichloromethane) afforded the title compound as a solid.

후처리

  1. customthe resultant reaction mixture
  2. extractionextracted with dichloromethane (3×)
  3. washThe combined dichloromethane layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customPurification by column chromatography (silica gel, 0-2% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-b39ceac2e98e4a5a9e200dfbd44192c7
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051290B2

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