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Pyridine → 20-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha, 2alpha-epoxypregna-5,7-dien-3beta-yl acetate

HRID 1196325
ノート
印刷プレビュー

反応式

HRID 1196325 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](O)[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]2[O:22][CH2:21][C:20]([CH3:24])([CH3:23])[CH2:19][O:18]2)[CH3:16])[CH2:6]1)(=[O:3])[CH3:2].N1C=CC=CC=1.CS(Cl)(=O)=O.C(OCC)(=O)C.CCCCCC>CN(C)C1C=CN=CC=1.C(Cl)Cl>[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][CH:9]=[C: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]2[O:18][CH2:19][C:20]([CH3:24])([CH3:23])[CH2:21][O:22]2)[CH3:16])[CH2:6]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 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 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 8674580520-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha, 2alpha-epoxypregna-5,7-dien-3beta-yl acetate収率 54.2%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a mixture of 49.0 mg (0.1 mmole) of 20-(5,5-di-methyl-1,3-dioxan-2-yl)-1α,2α-epoxy-7α-hydroxypregn-5-en-3β-yl acetate, 0.24 ml (3 mmoles) of pyridine, 0.5 mg (0.004 mmole) of 4-(dimethylamino)pyridine and 10 ml of methylene chloride was added 0.10 ml (1.3 mmoles) of methanesulfonyl chloride dropwise at a temperature of 0° C. and the mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted with 20 ml of methylene chloride, then washed successively with cold 1N-hydrochloric acid, water, aqueous sodium hydrogen carbonate solution and aqueous sodium chloride solution, and dried over magnesium sulfate. The solvent was then distilled off under reduced pressure. Finally the residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1:10, v/v) to give 25.5 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregna-5,7-dien-3β-yl acetate (yield: 54%). The 1H-NMR spectrum of this product was in agreement with that of the 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregna-5,7-dien-3β-yl acetate obtained in Example 17.

後処理

  1. washwashed successively with cold 1N-hydrochloric acid, water, aqueous sodium hydrogen carbonate solution and aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. distillationThe solvent was then distilled off under reduced pressure
  4. customFinally the residue was purified by silica gel chromatography (eluent

出典と根拠

ORDレコード
ord-3c8e1b4b58b7428a8050296636207402
出典データセット
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05112998

反応ノート

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