Sodium Acetate → 1-BOC-5-acetoxymethyl-7-nitro-indole-2-carboxylic acid methyl ester

HRID 1515249노트

반응식

HRID 1515249 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([CH2:14]Br)=[CH:9][C:8]=2[N+:16]([O-:18])=[O:17])=[O:4].[C:26]([O-:29])(=[O:28])[CH3:27].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([CH2:14][O:29][C:26](=[O:28])[CH3:27])=[CH:9][C:8]=2[N+:16]([O-:18])=[O:17])=[O:4]

참가 물질

4

반응물 2

HCID 517045Sodium AcetateHCID 594480901-BOC-5-bromomethyl-7-nitro-indole-2-carboxylic acid methyl ester

생성물 1

HCID 594480931-BOC-5-acetoxymethyl-7-nitro-indole-2-carboxylic acid methyl ester수율 50%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

1-BOC-5-bromomethyl-7-nitro-indole-2-carboxylic acid methyl ester (10.0 g, 24.2 mmol) prepared in Step B of Preparation 37 was dissolved in N,N-dimethylformamide (50 mL). Sodium acetate (2.4 g, 29.0 mmol) was added thereto, and the mixture was stirred for 4 h at room temperature. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The residue was purified by column chromatography to give the title compound (4.7 g, Yield 50%).

후처리

  1. customAfter completion of the reaction
  2. customthe solvent was removed by distillation under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-4de458094bbe4863ac87249afa10144a
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222414B2

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