Water → (2beta,3alpha,5alpha)-21-(Acetyloxy)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnan-20-one

HRID 233509노트

반응식

HRID 233509 반응식
[C:1]([O-:4])(=[O:3])[CH3:2].[K+].[OH:6][C@@H:7]1[C@@H:31]([N:32]2[CH2:37][CH2:36][O:35][C:34]([CH3:39])([CH3:38])[CH2:33]2)[CH2:30][C@@:29]2([CH3:40])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:41])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:17](=[O:24])[CH2:18]OS(C)(=O)=O)[CH2:8]1.O>C(O)C>[C:1]([O:4][CH2:18][C:17](=[O:24])[C@@H:16]1[C@:25]2([CH3:41])[C@H:13]([C@H:12]3[C@H:28]([CH2:27][CH2:26]2)[C@:29]2([CH3:40])[C@H:9]([CH2:8][C@H:7]([OH:6])[C@@H:31]([N:32]4[CH2:37][CH2:36][O:35][C:34]([CH3:39])([CH3:38])[CH2:33]4)[CH2:30]2)[CH2:10][CH2:11]3)[CH2:14][CH2:15]1)(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 517044Potassium AcetateHCID 10673665HCID 10673665, 화합물

생성물 1

HCID 10577010(2beta,3alpha,5alpha)-21-(Acetyloxy)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnan-20-one수율 35.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Anhydrous potassium acetate (470 mg) was added to (2β,3α,5α)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)-21-[(methylsulfonyl)oxy]pregnan-20-one (1.0 g) in ethanol (15 ml) and the solution was heated under reflux for 1.5 h. The reaction mixture was poured into water (150 ml) and the precipitated solid was filtered off, washed with water and the solid was 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-(acetyloxy)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnan-20-one (330 mg). m.p. 174°-175° C.; [α]D +13.9° (c 0.5).

후처리

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 1.5 h
  3. filtrationthe precipitated solid was filtered off
  4. washwashed with water
  5. dissolutionthe solid was dissolved in dichloromethane
  6. dry with materialAfter drying the solution over sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customthe residue was chromatographed on silica gel
  9. customThe purified product was crystallised from methanol

출처 및 근거

ORD 기록
ord-5917f1fd612d454ea1088ee8daca277b
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05593983

반응 노트

불러오는 중…