1-Acetoxy-2-bromoethane → 2-{4-(1,3-benzodioxol-5-yl)-5-methoxy-3-[(methoxymethyl)(phenethylsulfonyl)amino]-1H-pyrazol-1-yl}ethyl Acetate

HRID 1368663ノート

反応式

HRID 1368663 の反応式
[H-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[C:13]([O:32][CH3:33])=[N:14][NH:15][C:16]=3[N:17]([CH2:29][O:30][CH3:31])[S:18]([CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:20])=[O:19])=[CH:11][C:6]=2[O:5][CH2:4]1.[C:34]([O:37][CH2:38][CH2:39]Br)(=[O:36])[CH3:35]>O1CCCC1>[C:34]([O:37][CH2:38][CH2:39][N:14]1[C:13]([O:32][CH3:33])=[C:12]([C:10]2[CH:9]=[CH:8][C:7]3[O:3][CH2:4][O:5][C:6]=3[CH:11]=2)[C:16]([N:17]([CH2:29][O:30][CH3:31])[S:18]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:20])=[O:19])=[N:15]1)(=[O:36])[CH3:35]

参加物

5

反応物 3

HCID 135641-Acetoxy-2-bromoethane2 回HCID 24758Sodium hydride2 回HCID 22282022N-[4-(1,3-benzodioxol-5-yl)-3-methoxy-1H-pyrazol-5-yl]-N-(methoxymethyl)-2-phenyl-1-ethanesulfonamide

生成物 1

HCID 222819772-{4-(1,3-benzodioxol-5-yl)-5-methoxy-3-[(methoxymethyl)(phenethylsulfonyl)amino]-1H-pyrazol-1-yl}ethyl Acetate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (60% dispersion in oil, 162 mg) was added at room temperature under an atmosphere of nitrogen to a solution of N-[4-(1,3-benzodioxol-5-yl)-3-methoxy-1H-pyrazol-5-yl]-N-(methoxymethyl)-2-phenyl-1-ethanesulfonamide (Preparation 55) in anhydrous tetrahydrofurane. After 10 minutes, 2-bromoethyl acetate (446 μl) was added and the reaction mixture was refluxed overnight. At room temperature, some more 2-bromoethylacetate (446 μl) was added and the reaction was refluxed for 24 h. Then at room temperature, some more sodium hydride (50 mg) was added and the reaction was refluxed for 24 h. At room temperature, the reaction was quenched by the addition of an aqueous saturated solution of ammonium chloride (5 ml), water (10 ml) and the mixture was extracted with ethyl acetate (3×10 ml). The combined organic fractions were washed with brine (20 ml), dried on sodium sulfate and concentrated under reduced pressure to yield a dark oil which was purified by column chromatography (silica, 10 g), eluted with hexane:ethyl acetate (4:1) then (2:1) yielding the title compound as a colourless oil (92 mg).

後処理

  1. temperaturethe reaction mixture was refluxed overnight
  2. temperaturethe reaction was refluxed for 24 h
  3. temperaturethe reaction was refluxed for 24 h
  4. customAt room temperature, the reaction was quenched by the addition of an aqueous saturated solution of ammonium chloride (5 ml), water (10 ml)
  5. extractionthe mixture was extracted with ethyl acetate (3×10 ml)
  6. washThe combined organic fractions were washed with brine (20 ml)
  7. customdried on sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto yield a dark oil which
  10. customwas purified by column chromatography (silica, 10 g)
  11. washeluted with hexane:ethyl acetate (4:1)

出典と根拠

ORDレコード
ord-ed44b6e0ce26488ba75451a115a462ef
出典データセット
uspto-grants-2003_06
特許番号
US06573270B1

反応ノート

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