p-Toluenesulfonic acid monohydrate → HCID 68957642、化合物

HRID 2378046ノート

反応式

HRID 2378046 の反応式
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:18]([C:27]3([C:30]([O:32][CH3:33])=[O:31])[CH2:29][CH2:28]3)(O)[O:17][N:16]=2)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:33][O:32][C:30]([C:27]1([C:18]2[O:17][N:16]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3])=[CH:10][CH:11]=3)[C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:28][CH2:29]1)=[O:31]

参加物

5

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 68957797HCID 68957797、化合物2 回

生成物 1

HCID 68957642HCID 68957642、化合物

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6212Chloroform溶媒

反応条件

温度
80 °C

実験手順

Methyl 1-[3-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-5-hydroxy-4-phenyl-4,5-dihydroisoxazol-5-yl]cyclopropanecarboxylate (Compound C, 42 g) is dissolved in toluene (100 mL) and p-toluenesulfonic acid hydrate (1.7 g) is added with swirling. The mixture is heated over a steam bath until the internal mixture temperature, measured with a digital thermometer, is raised to 80° C. The mixture is then removed from the steam bath and is treated with water (50 mL.) The layers are shaken and separated and the toluene phase is dried over anhydrous magnesium sulfate and is concentrated under reduced pressure to afford an oil that is purified by flash silica gel column chromatography. Elution through a 400 g Analogix silica cartridge with a gradient (100% hexanes to 35% ethyl acetate over 1800 mL, or three column volumes) afforded an oily product. The product is dissolved in chloroform and is reconcentrated under reduced pressure to afford a residue that solidified overnight under high vacuum to the solid product (32 g.)

後処理

  1. temperatureThe mixture is heated over a steam bath until the internal mixture temperature
  2. customThe mixture is then removed from the steam bath
  3. additionis treated with water (50 mL.) The layers
  4. customseparated
  5. dry with materialthe toluene phase is dried over anhydrous magnesium sulfate
  6. concentrationis concentrated under reduced pressure
  7. customto afford an oil that
  8. customis purified by flash silica gel column chromatography
  9. washElution through a 400 g Analogix silica cartridge with a gradient (100% hexanes to 35% ethyl acetate over 1800 mL, or three column volumes)
  10. customafforded an oily product
  11. customto afford a residue that solidified overnight under high vacuum to the solid product (32 g.)

出典と根拠

ORDレコード
ord-e0c7d75860b7422f9b41cbb410225a1a
出典データセット
uspto-grants-2008_12
特許番号
US07470715B2

反応ノート

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