Lithium Hydroxide → HCID 57418674, compound

HRID 2114404Notes

Reaction equation

HRID 2114404 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9](=[O:11])[N:8]([CH2:12][C:13]([O:15]CC)=[O:14])[C:7]=2[CH:18]=1.[Li+].[OH-].CC#N.O.FC(F)(F)C(O)=O>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9](=[O:11])[N:8]([CH2:12][C:13]([OH:15])=[O:14])[C:7]=2[CH:18]=1

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 18373917Acetonitrile--water (1/1)HCID 57437815HCID 57437815, compound

Product 1

HCID 57418674HCID 57418674, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl [5-(methyloxy)-2-oxo-1,3-benzoxazol-3(2H)-yl]acetate (0.98 g, 3.9 mmol) was dissolved in 12.5 mL of tetrahydrofuran and treated with a solution of LiOH (0.094 g, 3.9 mmol) dissolved in 1.25 mL of water. The reaction was stirred vigorously at room temperature for 18 hours before it was determined to be complete by LCMS (two Aquasil C18, 20×1 mm columns were run in sequence, 4 minutes at 0.1 1 mL/min, 1-99% CH3CN/H2O with 0.018% trifluoroacetic acid, ES) Rt=1.5 min and m/e 224 [M+1]+. The solvent was removed by rotary evaporation and the residue was then dissolved in 100 mL of ethyl acetate. The organic layer was washed with a 10% hydrochloric acid solution (3×30 mL) and the organic phase was then dried over Na2SO4, filtered and concentrated to give [5-(methyloxy)-2-oxo-1,3-benzoxazol-3(2H)-yl]acetic acid (0.64 g, 2.8 mmol, 73%) as a brown amorphous solid. MS (ES) m/e 224 [M+H]+.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. dissolutionthe residue was then dissolved in 100 mL of ethyl acetate
  3. washThe organic layer was washed with a 10% hydrochloric acid solution (3×30 mL)
  4. dry with materialthe organic phase was then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dc825a9970f747beb84c4d8874815bcd
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

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