Lithium Hydroxide → HCID 57488865, compound

HRID 2114407Notes

Reaction equation

HRID 2114407 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]([O:10]CC)=[O:9])[C:5]2[CH:13]=[C:14]([O:17][C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:16][C:4]=2[O:3]1.[Li+].[OH-].CC#N.O.FC(F)(F)C(O)=O>O1CCCC1.O>[O:1]=[C:2]1[N:6]([CH2:7][C:8]([OH:10])=[O:9])[C:5]2[CH:13]=[C:14]([O:17][C:18]([F:21])([F:19])[F:20])[CH:15]=[CH:16][C:4]=2[O:3]1

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 18373917Acetonitrile--water (1/1)HCID 57488864Ethyl[2-oxo-5-[(trifluoromethyl)oxy]-1,3-benzoxazol-3(2H)-yl]acetate

Product 1

HCID 57488865HCID 57488865, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl [2-oxo-5-[(trifluoromethyl)oxy]-1,3-benzoxazol-3(2H)-yl]acetate (0.96 g, 3.0 mmol) was dissolved in 10 mL of tetrahydrofuran and treated with a solution of LiOH (0.083 g, 3.5 mmol) dissolved in 1.0 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=2.3 min and m/e 278 [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 under vacuum. The crude residue was purified by prep HPLC (Phenomenex, 30×75 mm, 40 mL/min, A: acetonitrile (0.1% TFA) B: water (0.1% TFA), A: 10 to 99% over 15 min, UV detection at 214 nm) to give [2-oxo-5-[(trifluoromethyl)oxy]-1,3-benzoxazol-3(2H)-yl]acetic acid (0.39 g, 1.4 mmol, 47%) as an off-white amorphous solid. MS (ES) m/e 278 [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 under vacuum
  7. customThe crude residue was purified by prep HPLC (Phenomenex, 30×75 mm, 40 mL/min
  8. waitA: acetonitrile (0.1% TFA) B: water (0.1% TFA), A: 10 to 99% over 15 min

Sources & evidence

ORD record
ord-2461414da289448c9e0d65eadf38d5cb
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

Loading…