盐酸 → (3beta,20S)-pregn-5-ene-3,20-diol 20-acetate

HRID 1069052笔记

反应方程式

HRID 1069052 反应方程式
[C:1]([O:4][C@H:5]([C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([CH2:22][CH2:23]2)[C@:19]2([CH3:20])[C:14]([CH2:15][C@@H:16]([O:26]C(OCC)C)[CH2:17][CH2:18]2)=[CH:13][CH2:12]3)[CH2:9][CH2:8]1)[CH3:6])(=[O:3])[CH3:2].Cl.O.C(=O)([O-])O.[Na+]>CC(C)=O>[C:1]([O:4][C@H:5]([C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([CH2:22][CH2:23]2)[C@:19]2([CH3:20])[C:14]([CH2:15][C@@H:16]([OH:26])[CH2:17][CH2:18]2)=[CH:13][CH2:12]3)[CH2:9][CH2:8]1)[CH3:6])(=[O:3])[CH3:2]

参与物

6

反应物 4

HCID 313盐酸HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 516892碳酸氢钠HCID 57200658(3beta,20S)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-ol acetate

产物 1

HCID 21969303(3beta,20S)-pregn-5-ene-3,20-diol 20-acetate收率 97.1%

试剂、催化剂与溶剂 1

HCID 180丙酮溶剂

实验过程

iv)—A solution of (3β,20S)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-ol acetate (66.1 g) in acetone (1330 ml) was treated with a 4 M aqueous solution of hydrochloric acid (13.2 ml). The reaction mixture was stirred for 45 minutes and subsequently poured into a mixture of water (3 l) and a saturated aqueous solution of sodium hydrogen carbonate (500 ml). The resulting precipitate was collected by filtration and then dissolved in dichloromethane. The filtrate was extracted with ethyl acetate. The dichloromethane and ethyl acetate solutions were washed with a saturated aqueous solution of sodium hydrogen carbonate and with brine, dried over sodium sulfate, and concentrated under reduced pressure to give (3β,20S)-pregn-5-ene-3,20-diol 20-acetate (compound 5a; 53.5 g), which was used in the following step without further purification.

后处理

  1. filtrationThe resulting precipitate was collected by filtration
  2. dissolutiondissolved in dichloromethane
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washThe dichloromethane and ethyl acetate solutions were washed with a saturated aqueous solution of sodium hydrogen carbonate and with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

来源与证据

ORD记录
ord-d4ffeb5118bc49da9475dd673fd2669d
来源数据集
uspto-grants-2001_06
专利号
US06251887B1

反应笔记

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