Lithium Hydroxide → HCID 57457166, Verbindung

HRID 2354398Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2354398
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

Komponenten

7

Edukt 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

Produkt 1

HCID 57457166HCID 57457166, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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]+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c78bb04d79a440709de26d4a711020bc
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07749998B2

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