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

HRID 82191Notes

Reaction equation

HRID 82191 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8c8627bc691c4bb58818f1b9ffa9ea8c
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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