Hydrochloric Acid → (2beta,3alpha,5alpha)-21-Chloro-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione

HRID 233494ノート

反応式

HRID 233494 の反応式
ClN1C(=[O:7])CCC1=O.[OH:9][C@@H:10]1[C@@H:32]([N:33]2[CH2:38][CH2:37][O:36][C:35]([CH3:40])([CH3:39])[CH2:34]2)[CH2:31][C@@:30]2([CH3:41])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:29]2[C:28](=[O:42])[CH2:27][C@@:26]2([CH3:43])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C:20](=NCCO)[CH3:21])[CH2:11]1.[ClH:44].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O>[Cl:44][CH2:21][C:20](=[O:7])[C@@H:19]1[C@:26]2([CH3:43])[C@H:16]([C@H:15]3[C@H:29]([C:28](=[O:42])[CH2:27]2)[C@:30]2([CH3:41])[C@H:12]([CH2:11][C@H:10]([OH:9])[C@@H:32]([N:33]4[CH2:38][CH2:37][O:36][C:35]([CH3:39])([CH3:40])[CH2:34]4)[CH2:31]2)[CH2:13][CH2:14]3)[CH2:17][CH2:18]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 31398ChlorosuccinimideHCID 86750168(2beta,3alpha,5alpha)-3-Hydroxy-20-[(2-hydroxyethyl)imino]-2-(2,2-dimethyl-4-morpholinyl)pregnan-11-one

生成物 1

HCID 10672358(2beta,3alpha,5alpha)-21-Chloro-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

N-Chlorosuccinimide (2.16 g) was added to a solution of (2β,3α,5α)-3-hydroxy-20-[(2-hydroxyethyl)imino]-2-(2,2-dimethyl-4-morpholinyl)pregnan-11-one (8.77 g) in tetrahydrofuran (175 ml). The solution was stirred at room temperature for 2 h and hydrochloric acid (53 ml; 1M) was then added. After stirring at room temperature for 1.25 h, the reaction mixture was poured into water (1 l). The pH was adjusted to 9 with aqueous sodium carbonate and the precipitated solid was filtered off, washed with water and dissolved in dichloromethane. After drying over sodium sulfate, the solvent was removed under reduced pressure and the residue was chromatographed on silica gel. The purified product was crystallised from diethyl ether to give (2β,3α,5α)-21-chloro-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione (3.23 g). m.p. 206°-208° C. (dec); [α]D +130.5° (c 0.57).

後処理

  1. stirringAfter stirring at room temperature for 1.25 h
  2. filtrationthe precipitated solid was filtered off
  3. washwashed with water
  4. dissolutiondissolved in dichloromethane
  5. dry with materialAfter drying 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-b045a551b7044123b5b4f767142570fa
出典データセット
uspto-grants-1997_01
特許番号
US05593983

反応ノート

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