20-(5,5-dimethyl-1,3-dioxan-2-yl)-1alpha-(tert-butyldimethylsilyl)oxy-3beta-(N,N-dimethylcarbamoyl)oxypregn-6-en-5alpha-ol → 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1alpha-(tert-butyldimethylsilyl)oxy-3beta-(N,N-dimethylcarbamoyl)oxypregna-5,7-diene
Reaction equation
[CH3:1][C:2]1([CH3:44])[CH2:7][O:6][CH:5]([CH:8]([C@@H:10]2[C@:27]3([CH3:28])[C@H:13]([C@H:14]4[C@H:24]([CH2:25][CH2:26]3)[C@:22]3([CH3:23])[C@:17](O)([CH2:18][C@@H:19]([O:37][C:38](=[O:42])[N:39]([CH3:41])[CH3:40])[CH2:20][C@@H:21]3[O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH:16]=[CH:15]4)[CH2:12][CH2:11]2)[CH3:9])[O:4][CH2:3]1>C1C=CC=CC=1.S(=O)(=O)(O)O>[CH3:44][C:2]1([CH3:1])[CH2:3][O:4][CH:5]([CH:8]([C@@H:10]2[C@:27]3([CH3:28])[C@H:13]([C:14]4[C@H:24]([CH2:25][CH2:26]3)[C@:22]3([CH3:23])[C:17]([CH2:18][C@@H:19]([O:37][C:38](=[O:42])[N:39]([CH3:41])[CH3:40])[CH2:20][C@@H:21]3[O:29][Si:30]([C:33]([CH3:34])([CH3:35])[CH3:36])([CH3:32])[CH3:31])=[CH:16][CH:15]=4)[CH2:12][CH2:11]2)[CH3:9])[O:6][CH2:7]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
In 10 ml of benzene was dissolved 350 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α-(tert-butyldimethylsilyl)oxy-3β-(N,N-dimethylcarbamoyl)oxypregn-6-en-5α-ol, followed by addition of one drop of concentrated sulfuric acid. The mixture was stirred in an atmosphere of argon gas under ice-cooling for 1 hour. The reaction mixture was then worked up in the same manner as Example 124 to give 135 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α-(tert-butyldimethylsilyl)oxy-3β-(N,N-dimethylcarbamoyl)oxypregna-5,7-diene showing the following properties.
Workup
- temperaturecooling for 1 hour
Sources & evidence
- ORD record
- ord-e31da403dcc64a6d9fc911cc08dcb15d
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05112998
Reaction notes
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