Lithium Hydroxide → HCID 57457166、化合物

HRID 2354398ノート

反応式

HRID 2354398 の反応式
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

参加物

7

反応物 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

生成物 1

HCID 57457166HCID 57457166、化合物収率 91%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-c78bb04d79a440709de26d4a711020bc
出典データセット
uspto-grants-2010_07
特許番号
US07749998B2

反応ノート

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