p-Toluenesulfonic acid → 1alpha-(tert-butyldimethylsilyl)oxy-3beta-(N,N-dimethylcarbamoyl)oxypregna-5,7-diene-20-carbaldehyde

HRID 1196386Notes

Reaction equation

HRID 1196386 reaction equation
CC1(C)CO[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]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])=[CH:16][CH:15]=4)[CH2:12][CH2:11]2)[CH3:9])[O:4]C1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[Si:30]([O:29][C@@H:21]1[C@@:22]2([CH3:23])[C:17](=[CH:16][CH:15]=[C:14]3[C@@H:24]2[CH2:25][CH2:26][C@@:27]2([CH3:28])[C@H:13]3[CH2:12][CH2:11][C@@H:10]2[CH:8]([CH:5]=[O:4])[CH3:9])[CH2:18][C@@H:19]([O:37][C:38](=[O:42])[N:39]([CH3:41])[CH3:40])[CH2:20]1)([C:33]([CH3:36])([CH3:34])[CH3:35])([CH3:32])[CH3:31]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 5725493220-(5,5-dimethyl-1,3-dioxan-2-yl)-1alpha-(tert-butyldimethylsilyl)oxy-3beta-(N,N-dimethylcarbamoyl)oxypregna-5,7-diene

Product 1

HCID 867458351alpha-(tert-butyldimethylsilyl)oxy-3beta-(N,N-dimethylcarbamoyl)oxypregna-5,7-diene-20-carbaldehydeYield 66.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 10 ml of acetone was dissolved 110 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α-(tert-butyldimethylsilyl)oxy-3β-(N,N-dimethylcarbamoyl)oxypregna-5,7diene, followed by addition of 10 mg of p-toluenesulfonic acid. The mixture was refluxed in an atmosphere of argon gas for 4 hours. The reaction mixture was then worked up in the same manner as Example 156 to give 63 mg of 1α-(tert-butyldimethylsilyl)oxy-3β-(N,N-dimethylcarbamoyl)oxypregna-5,7-diene-20-carbaldehyde showing the following physical properties.

Workup

  1. temperatureThe mixture was refluxed in an atmosphere of argon gas for 4 hours

Sources & evidence

ORD record
ord-f2a747c56e45420797899ace1a1f00f2
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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