Dehydroepiandrosterone → 3Betabenzyloxycarbonyloxy-5androsten-17-one

HRID 362768

反応式

HRID 362768 の反応式
[CH3:1][C@@:2]12[C:10](=[O:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH:13]=[C:14]3[CH2:19][C@@H:18]([OH:20])[CH2:17][CH2:16][C@:15]3([CH3:21])[C@H:5]1[CH2:4][CH2:3]2.[CH2:22]([O:29][C:30](Cl)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:22]([O:29][C:30]([O:20][C@H:18]1[CH2:17][CH2:16][C@@:15]2([CH3:21])[C:14](=[CH:13][CH2:12][C@@H:6]3[C@@H:5]2[CH2:4][CH2:3][C@@:2]2([CH3:1])[C@H:7]3[CH2:8][CH2:9][C:10]2=[O:11])[CH2:19]1)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

4

反応物 2

HCID 5881DehydroepiandrosteroneHCID 10387Benzyl chloroformate

生成物 1

HCID 542344703Betabenzyloxycarbonyloxy-5androsten-17-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of dehydroepiandrosterone (2.88 g, 10 mmol) in methylene chloride (100 mL) is added dropwise benzylchloroformate, over a period of 30 min following the known procedure (F. Reber and T. Reichstein, Helv. Chim. Acta, 28, 1164, 1945). After stirring for 3 h, the mixture is washed with water and evaporated to dryness. The residue is then dissolved in acetone and precipitated in iced water. After 16 h, crystals are filtered and dried in vacuo.

後処理

  1. washthe mixture is washed with water
  2. customevaporated to dryness
  3. dissolutionThe residue is then dissolved in acetone
  4. customprecipitated in iced water
  5. waitAfter 16 h
  6. filtrationcrystals are filtered
  7. customdried in vacuo

出典と根拠

ORDレコード
ord-acb57084100a4b42b0135c42120e0ae5
出典データセット
uspto-grants-1999_02
特許番号
US05872114

関連ノート

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