Acetohydroxamic Acid → (3-Amino-benzo[d]isoxazol-5-yl)-acetic acid ethyl ester

HRID 82191ノート

反応式

HRID 82191 の反応式
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=C[C:9](F)=[C:8](C#N)[CH:7]=1)[CH3:2].[C:16]([NH:19][OH:20])(=O)[CH3:17].C(=O)([O-])[O-].[K+].[K+].C[N:28](C=O)C>O>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[O:20][N:19]=[C:16]([NH2:28])[C:17]=2[CH:11]=1)[CH3:2]

参加物

6

反応物 4

HCID 1990Acetohydroxamic AcidHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 70817504(3-Cyano-4-fluoro-phenyl)-acetic acid ethyl ester

生成物 1

HCID 70817110(3-Amino-benzo[d]isoxazol-5-yl)-acetic acid ethyl ester収率 59%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

To a solution of (3-cyano-4-fluoro-phenyl)-acetic acid ethyl ester (Preparation 127, 400 mg, 1.93 mmol) and acetohydroxamic acid (362 mg, 4.83 mmol) in DMF (40 mL) and water (15 mL) was added potassium carbonate (1.6 g, 11.58 mmol) and the reaction mixture stirred at room temperature for 12 hours. The reaction mixture was diluted with water (100 mL) and the resulting white precipitate and collected by filtration. The crude material was purified by silica gel column chromatography eluting with a gradient of dichloromethane:methanol 100:0 to 97:3 to afford the title compound as an off-white solid in 59% yield, 250 mg.

後処理

  1. filtrationthe resulting white precipitate and collected by filtration
  2. customThe crude material was purified by silica gel column chromatography
  3. washeluting with a gradient of dichloromethane:methanol 100:0 to 97:3

出典と根拠

ORDレコード
ord-8c8627bc691c4bb58818f1b9ffa9ea8c
出典データセット
uspto-grants-2014_09
特許番号
US08846698B2

反応ノート

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