Cesium carbonate → 5-tert-butoxycarbonylmethoxy-1H-indole-2-carboxylic acid ethyl ester

HRID 1790897

反応式

HRID 1790897 の反応式
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([OH:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2].Br[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 90677Ethyl 5-hydroxy-1H-indole-2-carboxylate

生成物 1

HCID 695874395-tert-butoxycarbonylmethoxy-1H-indole-2-carboxylic acid ethyl ester収率 63%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 5-hydroxy-1H-indole-2-carboxylic acid ethyl ester (2 g, 10 mmol), tert-butyl bromoacetate (2.35 g, 12 mmol) and cesium carbonate (10.5 g, 30 mmol) in dimethylformamide (10 mL) was stirred at room temperature for 16 hours. The reaction was diluted with ethyl acetate (150 mL), washed with water (5×50 mL) and brine, dried and concentrated. The residue was recrystallized from ethyl acetate and hexane to give 2 g (63%) 5-tert-butoxycarbonylmethoxy-1H-indole-2-carboxylic acid ethyl ester.

後処理

  1. washwashed with water (5×50 mL) and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was recrystallized from ethyl acetate and hexane

出典と根拠

ORDレコード
ord-f06ef23162cf40829f6f7b12ee23801d
出典データセット
uspto-grants-2006_07
特許番号
US07071332B2

関連ノート

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