Water → 21-Chloro-17alpha-hydroxy-20-methoxypregna-4,9(11),20-trien-3-one

HRID 66550노트

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HRID 66550 반응식
[Cl:1][CH:2](S(C1C=CC=CC=1)=O)[C:3]([O:24][CH3:25])=[C:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C:18](=[CH:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.[OH-:34].[Na+].O.C(Cl)Cl>C1COCC1.CO.CC(C)=O>[Cl:1][CH:2]=[C:3]([O:24][CH3:25])[C@:4]1([OH:34])[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C:18](=[CH:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1

참가 물질

8

반응물 4

HCID 962WaterHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 5701252721-Chloro-20-methoxy-21-(phenylsulfinyl)pregna-4,9(11),17(20)-trien-3-one

생성물 1

HCID 8673851121-Chloro-17alpha-hydroxy-20-methoxypregna-4,9(11),20-trien-3-one

시약·촉매·용매 3

HCID 180Acetone용매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 21-chloro-20-methoxy-21-(phenylsulfinyl)pregna-4,9(11),17(20)-trien-3-one (VI, Example 3, 100 mg) in THF (2 ml), methanol (0.45 ml) and acetone (0.3 ml) at 0° under nitrogen is added a solution of sodium hydroxide (5 N, 0.04 ml). The mixture is brought to 20°-25° and is allowed to stir for 24 hr. The mixture is poured into a mixture of water (25 ml) and methylene chloride (10 ml). The layers are separated and the aqueous layer is extracted with methylene chloride (2×5 ml). The organic extracts are combined and washed with water (10 ml), dried over sodium sulfate and concentrated under reduced pressure to give the title compound.

후처리

  1. customis brought to 20°-25°
  2. customThe layers are separated
  3. extractionthe aqueous layer is extracted with methylene chloride (2×5 ml)
  4. washwashed with water (10 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-4e98e46d8be14dc0b62c0c3aef402f49
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04342702

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