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

HRID 82191

Reaktionsgleichung

Reaktionsgleichung von HRID 82191
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8c8627bc691c4bb58818f1b9ffa9ea8c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846698B2

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