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Sodium hydride → tert-butyl 3-[2-(acetyloxy)ethoxy]-5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-1-methyl-1H-pyrazole-4-carboxylate

HRID 1368639
ノート
印刷プレビュー

反応式

HRID 1368639 の反応式
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:11]([NH2:20])[N:10]([CH3:21])[N:9]=1)(=[O:3])[CH3:2].[H-].[Na+].[C:24]([C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1)([CH3:27])([CH3:26])[CH3:25].[Cl-].[NH4+]>O1CCCC1.O>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])=[C:11]([NH:20][S:34]([C:31]2[CH:32]=[CH:33][C:28]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:29][CH:30]=2)(=[O:36])=[O:35])[N:10]([CH3:21])[N:9]=1)(=[O:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 22281904tert-butyl 3-[2-(acetyloxy)ethoxy]-5-amino-1-methyl-1H-pyrazole-4-carboxylate

生成物 1

HCID 22282018tert-butyl 3-[2-(acetyloxy)ethoxy]-5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-1-methyl-1H-pyrazole-4-carboxylate収率 13.8%

試薬・触媒・溶媒

2
HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To tert-butyl 3-[2-(acetyloxy)ethoxy]-5-amino-1-methyl-1H-pyrazole-4-carboxylate (Preparation 10) (70 g) in solution in tetrahydrofuran (1 lit.) at 0° C. was added sodium hydride (20.2 g of a 60% dispersion in oil). The reaction mixture was stirred at room temperature for one hour and then 4-(tert-butyl)benzenesulfonyl chloride (58.88 g) was added dropwise. The reaction mixture was stirred at room temperature overnight and was then diluted with water (200 ml) at 0° C., followed by a saturated solution of ammonium chloride (200 ml) while allowing the mixture to warm to room temperature. The white precipitate was filtered off and disposed of. The aqueous and organic layers were separated and the aqueous extracted with ethyl acetate (100 ml). The combined organics were dried on magnesium sulfate, filtered and concentrated under reduced pressure. The crude was purified by chromatography on a suction column packed with silica eluted with ethyl acetate:hexane (1:4) to yield the desired product as white solid (16 g).

後処理

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. temperatureto warm to room temperature
  3. filtrationThe white precipitate was filtered off
  4. customThe aqueous and organic layers were separated
  5. extractionthe aqueous extracted with ethyl acetate (100 ml)
  6. customThe combined organics were dried on magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude was purified by chromatography on a suction column
  10. washeluted with ethyl acetate:hexane (1:4)

出典と根拠

ORDレコード
ord-86e09a393bf540f1acffb1b425808dea
出典データセット
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06573270B1

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート