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

HRID 66550ノート

反応式

HRID 66550 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4e98e46d8be14dc0b62c0c3aef402f49
出典データセット
uspto-grants-1982_08
特許番号
US04342702

反応ノート

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