Lithium Hydroxide → HCID 57488865、化合物

HRID 2354405ノート

反応式

HRID 2354405 の反応式
C([O:3][C:4](=[O:21])[CH2:5][N:6]1[C:10]2[CH:11]=[C:12]([O:15][C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:14][C:9]=2[O:8][C:7]1=[O:20])C.[Li+].[OH-].CC#N.O.FC(F)(F)C(O)=O>O1CCCC1.O>[O:20]=[C:7]1[N:6]([CH2:5][C:4]([OH:21])=[O:3])[C:10]2[CH:11]=[C:12]([O:15][C:16]([F:19])([F:17])[F:18])[CH:13]=[CH:14][C:9]=2[O:8]1

参加物

7

反応物 4

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

生成物 1

HCID 57488865HCID 57488865、化合物収率 47%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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 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]+.

後処理

  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

出典と根拠

ORDレコード
ord-4f45d8d6e7fa48a797180cb1b8d9ec37
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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