Water → 21-Chloro-17alpha-hydroxy-20-methoxypregna-4,9(11),20-trien-3-one
Reaction equation
[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]1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
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.
Workup
- customis brought to 20°-25°
- customThe layers are separated
- extractionthe aqueous layer is extracted with methylene chloride (2×5 ml)
- washwashed with water (10 ml)
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-4e98e46d8be14dc0b62c0c3aef402f49
- Source dataset
- uspto-grants-1982_08
- Patent number
- US04342702
Reaction notes
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