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Water → (2beta,3alpha,5alpha)-21-(Acetylthio)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione

HRID 233495
ノート
印刷プレビュー

反応式

HRID 233495 の反応式
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].Cl[CH2:7][C:8](=[O:38])[C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([C:24](=[O:28])[CH2:25]2)[C@:21]2([CH3:22])[C@H:16]([CH2:17][C@H:18]([OH:37])[C@@H:19]([N:29]4[CH2:34][CH2:33][O:32][C:31]([CH3:36])([CH3:35])[CH2:30]4)[CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1.O>C(O)C>[C:1]([S:3][CH2:7][C:8](=[O:38])[C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([C:24](=[O:28])[CH2:25]2)[C@:21]2([CH3:22])[C@H:16]([CH2:17][C@H:18]([OH:37])[C@@H:19]([N:29]4[CH2:34][CH2:33][O:32][C:31]([CH3:36])([CH3:35])[CH2:30]4)[CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)(=[O:4])[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

5

反応物 3

HCID 962WaterHCID 10672358(2beta,3alpha,5alpha)-21-Chloro-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dioneHCID 23670855Potassium ethanethioate

生成物 1

HCID 10577865(2beta,3alpha,5alpha)-21-(Acetylthio)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione収率 60.7%

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒

実験手順

Potassium thioacetate (1.32 g) was added to a solution of the 21-chloro-compound of Example 2 (2.22 g) in ethanol (11.1 ml). The mixture was heated under reflux in an atmosphere of nitrogen for 40 min and then poured into water (100 ml). The precipitated solid was filtered off, washed with water and dissolved in dichloromethane. After drying the solution over sodium sulfate the solvent was removed under reduced pressure and the residue was chromatographed on silica gel. The purified product was crystallised from methanol to give (2β,3α,5α)-21-(acetylthio)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione (1.46 g). m.p. 181°-182° C.; [α]D +131.9° (c 0.88).

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux in an atmosphere of nitrogen for 40 min
  3. filtrationThe precipitated solid was filtered off
  4. washwashed with water
  5. dissolutiondissolved in dichloromethane
  6. dry with materialAfter drying the solution over sodium sulfate the solvent
  7. customwas removed under reduced pressure
  8. customthe residue was chromatographed on silica gel
  9. customThe purified product was crystallised from methanol

出典と根拠

ORDレコード
ord-0ca7d4a6a93b480ba431d434203e08f8
出典データセット
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05593983

反応ノート

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