Ethyl Acetate → 2-[(5-{{[4-(tert-butyl)phenyl]sulfonyl}[(2-methoxyethoxy)methyl]amino)-4-iodo-1-methyl-1H-pyrazol-3-yl)oxy]ethyl acetate

HRID 1368643ノート

反応式

HRID 1368643 の反応式
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([I:13])=[C:11]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[N:10]([CH3:28])[N:9]=1)(=[O:3])[CH3:2].[H-].[Na+].[CH3:31][O:32][CH2:33][CH2:34][O:35][CH2:36]Cl.C(OCC)(=O)C>O1CCCC1.[Cl-].[NH4+]>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([I:13])=[C:11]([N:14]([S:15]([C:18]2[CH:19]=[CH:20][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[N:10]([CH3:28])[N:9]=1)(=[O:3])[CH3:2]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 222820342-{[5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-4-iodo-1-methyl-1H-pyrazol-3-yl)oxy}ethyl acetate

生成物 1

HCID 222818952-[(5-{{[4-(tert-butyl)phenyl]sulfonyl}[(2-methoxyethoxy)methyl]amino)-4-iodo-1-methyl-1H-pyrazol-3-yl)oxy]ethyl acetate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 25517Ammonium Chloride溶媒

実験手順

To 2-{[5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-4-iodo-1-methyl-1H-pyrazol-3-yl)oxy}ethyl acetate (Preparation 7) (8 g) in solution in tetrahydrofuran (200 ml) was added sodium hydride (860 mg of a 60% dispersion in oil), at room temperature. The reaction was stirred at room temperature for 0.5 hours and 2-methoxyethoxymethyl chloride (2.7 ml) was added dropwise. The reaction was stirred for an other 0.5 hours and was then diluted with a saturated aqueous solution of ammonium chloride (50 ml) and reduced under reduced pressure. Ethyl acetate (100 ml) was added and the organic layer separated. The organics were washed with brine (20 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by chromatography on a suction column packed with silica eluted with ethyl acetate:hexane (1:1) to yield the desired product as pale yellow oil (9.5 g).

後処理

  1. stirringThe reaction was stirred for an other 0.5 hours
  2. customthe organic layer separated
  3. washThe organics were washed with brine (20 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by chromatography on a suction column
  8. washeluted with ethyl acetate:hexane (1:1)

出典と根拠

ORDレコード
ord-28ce42951b8349b9af636d1dca3bfcb4
出典データセット
uspto-grants-2003_06
特許番号
US06573270B1

反応ノート

読み込み中…