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

HRID 233494노트

반응식

HRID 233494 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b045a551b7044123b5b4f767142570fa
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05593983

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