Dimethyl Carbonate → 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1alpha-(tert-butyldimethylsilyl)oxy-3beta-(N,N-dimethylcarbamoyl)oxy-7alpha-(methoxycarbonyl)oxypregn-5-ene

HRID 1196373Notes

Reaction equation

HRID 1196373 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.[C:45](=[O:50])([O:48]C)[O:46][CH3:47]>S(=O)(=O)(O)O>[CH3:44][C:2]1([CH3:1])[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]([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]([CH3:35])([CH3:36])[CH3:34])([CH3:31])[CH3:32])=[CH:16][C@H:15]4[O:50][C:45]([O:46][CH3:47])=[O:48])[CH2:12][CH2:11]2)[CH3:9])[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 12021Dimethyl CarbonateHCID 6785291120-(5,5-dimethyl-1,3-dioxan-2-yl)-1alpha-(tert-butyldimethylsilyl)oxy-3beta-(N,N-dimethylcarbamoyl)oxypregn-6-en-5alpha-ol

Product 1

HCID 2284392520-(5,5-dimethyl-1,3-dioxan-2-yl)-1alpha-(tert-butyldimethylsilyl)oxy-3beta-(N,N-dimethylcarbamoyl)oxy-7alpha-(methoxycarbonyl)oxypregn-5-ene

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

In 10 ml of dimethyl carbonate 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 132 to give 95 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α -(tert-butyldimethylsilyl)oxy-3β-(N,N-dimethylcarbamoyl)oxy-7α-(methoxycarbonyl)oxypregn-5-ene showing the following physical properties.

Workup

  1. temperaturecooling for 1 hour

Sources & evidence

ORD record
ord-0267794c2c15476297c58a827abb0b9a
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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