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

HRID 82191

반응식

HRID 82191 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8c8627bc691c4bb58818f1b9ffa9ea8c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846698B2

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