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

HRID 336458ノート

反応式

HRID 336458 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-31146877a1ec412aadf00028482fdb41
出典データセット
uspto-grants-2014_11
特許番号
US08889691B2

反応ノート

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