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Methanesulfonic Acid → (2beta,3alpha,5alpha)-3-Hydroxy-2-(2,2-dimethyl-4-morpholinyl)-21-thiocyanatopregnane-11,20-dione

HRID 233520
ノート
印刷プレビュー

反応式

HRID 233520 の反応式
Cl[CH2:2][C:3](=[O:33])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([C:19](=[O:23])[CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([CH2:12][C@H:13]([OH:32])[C@@H:14]([N:24]4[CH2:29][CH2:28][O:27][C:26]([CH3:31])([CH3:30])[CH2:25]4)[CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.CS(O)(=O)=O.[S-:39][C:40]#[N:41].[K+].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[OH:32][C@@H:13]1[C@@H:14]([N:24]2[CH2:29][CH2:28][O:27][C:26]([CH3:31])([CH3:30])[CH2:25]2)[CH2:15][C@@:16]2([CH3:17])[C@@H:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:18]2[C:19](=[O:23])[CH2:20][C@@:21]2([CH3:22])[C@H:7]3[CH2:6][CH2:5][C@@H:4]2[C:3](=[O:33])[CH2:2][S:39][C:40]#[N:41])[CH2:12]1
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 6395Methanesulfonic AcidHCID 10340Sodium CarbonateHCID 516872Potassium thiocyanateHCID 10672358(2beta,3alpha,5alpha)-21-Chloro-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione

生成物 1

HCID 10696819(2beta,3alpha,5alpha)-3-Hydroxy-2-(2,2-dimethyl-4-morpholinyl)-21-thiocyanatopregnane-11,20-dione収率 17.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒2 回

実験手順

To (2β,3α,5α)-21-chloro-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione (3.1 g) was added a solution of methanesulfonic acid (615 mg) in methanol (63 ml) and then a solution of potassium thiocyanate (12.4 g) in water (32 ml). The resulting solution was stirred at room temperature for 24 h, poured into water and sodium carbonate was then added until the pH exceeded 9. The precipitated solid was filtered off, washed with water and dissolved in dichloromethane. This solution was dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel and the purified product was crystallised from diethyl ether and then from methanol to give (2β,3α,5α)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)-21-thiocyanatopregnane-11,20-dione (572 mg). m.p. 197°-198° C.; [α]D +99.3° (c 0.8).

後処理

  1. additionwas then added until the pH
  2. filtrationThe precipitated solid was filtered off
  3. washwashed with water
  4. dissolutiondissolved in dichloromethane
  5. dry with materialThis solution was dried over sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was chromatographed on silica gel
  8. customthe purified product was crystallised from diethyl ether

出典と根拠

ORDレコード
ord-27159a280d9542989db8091d57903fca
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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このページの内容参加物実験手順後処理出典と根拠反応ノート