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Acetic Acid → 20-(5,5-Dimethyl-1,3-dioxan-2-yl)-3beta-(tert-butyldimethylsilyl)oxy-1alpha-(methoxymethyl)oxy-7alpha-(methoxycarbonyl)oxypregn-5-ene

HRID 1196374
Notes
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Reaction equation

HRID 1196374 reaction equation
[CH3:1][C:2]1([CH3:42])[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:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[CH2:20][C@@H:21]3[O:29][CH2:30][O:31][CH3:32])[CH:16]=[CH:15]4)[CH2:12][CH2:11]2)[CH3:9])[O:4][CH2:3]1.C(O)(=O)C.[C:47](=[O:52])([O:50]C)[O:48][CH3:49]>>[CH3:42][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:33][Si:34]([C:37]([CH3:38])([CH3:39])[CH3:40])([CH3:35])[CH3:36])[CH2:20][C@@H:21]3[O:29][CH2:30][O:31][CH3:32])=[CH:16][C@H:15]4[O:52][C:47]([O:48][CH3:49])=[O:50])[CH2:12][CH2:11]2)[CH3:9])[O:4][CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 12021Dimethyl CarbonateHCID 6785294620-(5,5-Dimethyl-1,3-dioxan-2-yl)-3beta-(tertbutyldimethylsilyl)oxy-1alpha-(methoxymethyl)oxypregn-6-en-5alpha-ol

Product 1

HCID 6785295620-(5,5-Dimethyl-1,3-dioxan-2-yl)-3beta-(tert-butyldimethylsilyl)oxy-1alpha-(methoxymethyl)oxy-7alpha-(methoxycarbonyl)oxypregn-5-ene

Procedure

In 10 ml of dimethyl carbonate was dissolved 400 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-3β-(tert-butyldimethylsilyl)oxy-1α-(methoxymethyl)oxypregn-6-en-5α-ol, followed by addition of 0.2 ml of acetic acid. The mixture was refluxed in an atmosphere of argon gas for 12 hours. The reaction mixture was then worked up in the same manner as Example 132 to give 120 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-3β-(tert-butyldimethylsilyl)oxy-1α-(methoxymethyl)oxy-7α-(methoxycarbonyl)oxypregn-5-ene showing the following physical properties.

Workup

  1. temperatureThe mixture was refluxed in an atmosphere of argon gas for 12 hours

Sources & evidence

ORD record
ord-10447b0204094d4d93fd10ccbd48ccf9
Source dataset
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05112998

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes