p-Toluenesulfonic acid → 3beta-Acetoxy-1alpha,2alpha-epoxy-7alpha-hydroxypregn-5-ene-20-carbaldehyde

HRID 1708773ノート

反応式

HRID 1708773 の反応式
[C:1]([O:4][C@H:5]1[C@@H:31]2[O:32][C@@H:30]2[C@@:29]2([CH3:33])[C:7](=[CH:8][C@@H:9]([OH:35])[C@@H:10]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:34])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[CH:15]([CH:17]2OCC(C)(C)C[O:18]2)[CH3:16])[CH2:6]1)(=[O:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C.CCCCCC>CC(C)=O>[C:1]([O:4][C@H:5]1[C@@H:31]2[O:32][C@@H:30]2[C@@:29]2([CH3:33])[C:7](=[CH:8][C@@H:9]([OH:35])[C@@H:10]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:34])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[CH:15]([CH:17]=[O:18])[CH3:16])[CH2:6]1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 21226206Ethyl acetate hexaneHCID 8674580220-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha, 2alpha-epoxy-7alpha-hydroxypregna-5-en-3beta-yl acetate

生成物 1

HCID 867458133beta-Acetoxy-1alpha,2alpha-epoxy-7alpha-hydroxypregn-5-ene-20-carbaldehyde収率 67.1%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

実験手順

In 4 ml of acetone was dissolved 4.9 mg (0.01 mmole) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxy-7α-hydroxypregna-5-en-3β-yl acetate, followed by addition of 1 ml of a 1 mmol/1 solution of p-toluenesulfonic acid in acetone (containing 0.001 mmole of p-toluenesulfonic acid). The mixture was stirred at room temperature for 12 hours. From the reaction mixture thus obtained, the solvent was distilled off under reduced pressure and the residue was diluted with methylene chloride. This methylene chloride solution was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel chromatography (eluent:ethyl acetate-hexane =1:5, v/v) to recover 2.7 mg of 3β-acetoxy-1α,2α-epoxy-7α-hydroxypregna-5-ene-20-carbaldehyde (yield: 67%).

後処理

  1. customFrom the reaction mixture thus obtained
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionthe residue was diluted with methylene chloride
  4. washThis methylene chloride solution was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customthe residue was purified by silica gel chromatography (eluent

出典と根拠

ORDレコード
ord-6aeec4984be0486b9af554a07cca6925
出典データセット
uspto-grants-1994_10
特許番号
US05359055

反応ノート

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