Cesium fluoride → N-(3,4-dimethyl-5-isoxazolyl)-2-(alpha-hydroxybenzyl)thiophene-3-sulfonamide

HRID 1738535ノート

反応式

HRID 1738535 の反応式
C[Si](C)(C)CCOC[C:7]1([CH:23]([OH:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:11]([S:12]([NH:15][C:16]2[O:20][N:19]=[C:18]([CH3:21])[C:17]=2[CH3:22])(=[O:14])=[O:13])[CH:10]=[CH:9][S:8]1.[F-].[Cs+]>CN(C=O)C>[CH3:21][C:18]1[C:17]([CH3:22])=[C:16]([NH:15][S:12]([C:11]2[CH:10]=[CH:9][S:8][C:7]=2[CH:23]([OH:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:14])=[O:13])[O:20][N:19]=1

参加物

4

反応物 2

HCID 25953Cesium fluorideHCID 22998524HCID 22998524、化合物

生成物 1

HCID 22998493N-(3,4-dimethyl-5-isoxazolyl)-2-(alpha-hydroxybenzyl)thiophene-3-sulfonamide収率 51%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 2-[2-(trimethylsilyl)ethoxymethyl]-N-(3,4-dimethyl-5-isoxazolyl)-2-(α-hydroxybenzyl)thiophene-3-sulfonamide (70 mg, 0-14 mmol) in DMF (2 ml) was added cesium fluoride (26 mg, 0.17 mmole) in one portion. The resulting mixture was heated to 100° C. for 10 hours. The solvents were removed by evaporation under vacuum and the remaining residue was extracted into ethyl acetate, washed with water, brine, and dried over MgSO4. The product was then purified by chromatography using 50-70% ethyl acetate/hexanes to give 26.2 mg N-(3,4-dimethyl-5-isoxazolyl)-2-(α-hydroxybenzyl)thiophene-3-sulfonamide as a pale white semisolid (51% yield).

後処理

  1. customThe solvents were removed by evaporation under vacuum
  2. extractionthe remaining residue was extracted into ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. customThe product was then purified by chromatography

出典と根拠

ORDレコード
ord-f96ab404406c42bc8ec44918112240c0
出典データセット
uspto-grants-1999_10
特許番号
US05962490

反応ノート

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