Lithium Hydroxide → HCID 57457166, compound

HRID 2354398Notes

Reaction equation

HRID 2354398 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][N:6]1[C:11]2[CH:12]=[C:13]([C:18]([F:21])([F:20])[F:19])[C:14]([O:16][CH3:17])=[CH:15][C:10]=2[O:9][CH2:8][C:7]1=[O:22])C.[Li+].[OH-].CC#N.O.FC(F)(F)C(O)=O>O1CCCC1.O>[CH3:17][O:16][C:14]1[C:13]([C:18]([F:21])([F:19])[F:20])=[CH:12][C:11]2[N:6]([CH2:5][C:4]([OH:23])=[O:3])[C:7](=[O:22])[CH2:8][O:9][C:10]=2[CH:15]=1

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 18373917Acetonitrile--water (1/1)HCID 57437814Ethyl[7-(methyloxy)-3-oxo-6-(trifluoromethyl)-2,3-dihydro-4H-1,4-benzoxazin-4-yl]acetate

Product 1

HCID 57457166HCID 57457166, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl[7-(methyloxy)-3-oxo-6-(trifluoromethyl)-2,3-dihydro-4H-1,4-benzoxazin-4-yl]acetate (0.36 g, 1.1 mmol) was dissolved in 4 mL of tetrahydrofuran and treated with a solution of LiOH (0.028 g, 1.2 mmol) dissolved in 0.5 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 mL/min, 1-99% CH3CN/H2O with 0.018% trifluoroacetic acid, ES) Rt=1.62 min and m/e 306 [M+1]+. The solvent was removed by rotary evaporation and the residue was then dissolved in 50 mL of ethyl acetate. The organic layer was washed with a 10% hydrochloric acid solution (3×10 mL) and the organic phase was then dried over Na2SO4, filtered and concentrated to give [7-(methyloxy)-3-oxo-6-(trifluoromethyl)-2,3-dihydro-4H-1,4-benzoxazin-4-yl]acetic acid (0.31 g, 1.0 mmol, 91%) as an off-white amorphous solid. MS (ES) m/e 306 [M+H]+.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. dissolutionthe residue was then dissolved in 50 mL of ethyl acetate
  3. washThe organic layer was washed with a 10% hydrochloric acid solution (3×10 mL)
  4. dry with materialthe organic phase was then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c78bb04d79a440709de26d4a711020bc
Source dataset
uspto-grants-2010_07
Patent number
US07749998B2

Reaction notes

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