Tetrahydrofuran → N-[5-(4-fluoro-phenyl)-isoxazol-3-yl]-malonamic acid

HRID 1665688Notes

Reaction equation

HRID 1665688 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:23])[CH2:7][C:8]([NH:10][C:11]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[O:13][N:12]=1)=[O:9])C.C1COCC1>O>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]2[O:13][N:12]=[C:11]([NH:10][C:8](=[O:9])[CH2:7][C:6]([OH:23])=[O:5])[CH:15]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57875802N-[5-(4-fluoro-phenyl)-isoxazol-3-yl]-malonamic acid ethyl ester

Product 1

HCID 57875816N-[5-(4-fluoro-phenyl)-isoxazol-3-yl]-malonamic acidYield 90.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

NaOH (34 mg, 8.5 mmol) was added to a solution of N-[5-(4-fluoro-phenyl)-isoxazol-3-yl]-malonamic acid ethyl ester (292 mg, 1.0 mmol) in the mixture of THF (13 mL) and H2O (13 mL) and stirred for 1 hr at room temperature. The reaction mixture was concentrated and the obtained residue was diluted with water, acidified with concentrated HCl, and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over Na2SO4 and concentrated to afford 40 mg (90.9% Yield) of N-[5-(4-fluoro-phenyl)-isoxazol-3-yl]-malonamic acid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe obtained residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bfdb5dd771a44f1695541b673278d3d2
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

Loading…