N,N-Dimethylacrylamide → HCID 69630482, compound

HRID 1792204Notes

Reaction equation

HRID 1792204 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@:29]2([CH3:30])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:31])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C:21]([OH:24])([CH3:23])[CH3:22])[CH2:12][C@@H:11]([O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:40][N:41]([CH3:46])[C:42](=[O:45])[CH:43]=[CH2:44].[H-].[Na+]>O1CCCC1>[Si:1]([O:8][C@@H:9]1[C@@:29]2([CH3:30])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:31])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C:21]([O:24][CH2:44][CH2:43][C:42]([N:41]([CH3:46])[CH3:40])=[O:45])([CH3:23])[CH3:22])[CH2:12][C@@H:11]([O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:34])[CH3:35])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 17587N,N-DimethylacrylamideHCID 24758Sodium hydrideHCID 696299251alpha,3beta-Bis(tert-butyldimethylsilyloxy)-20-hydroxy-20-methylpregna-5,7,16-triene

Product 1

HCID 69630482HCID 69630482, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1α,3β-Bis(tert-butyldimethylsilyloxy)-20-hydroxy-20-methylpregna-5,7,16-triene (200 mg, 0.36 mmol), N,N-dimethylacrylamide (107 mg, 1.08 mmol), sodium hydride (60% in oil, 23 mg, 0.56 mmol) and tetrahydrofuran (4 ml) were subjected to reaction using a procedure similar to that of Example 25(1) (17 hours at room temperature), worked up and purified by preparative thin layer chromatography (4 sheets (each 1.0 mm thickness), ethyl acetate) to give the titled compound (114 mg, 47.1%) as white powder.

Workup

  1. customof Example 25(1) (17 hours at room temperature)
  2. custompurified by preparative thin layer chromatography (4 sheets (each 1.0 mm thickness), ethyl acetate)

Sources & evidence

ORD record
ord-57fc10183ae24c289d5d5e52fdec0be2
Source dataset
uspto-grants-2006_07
Patent number
US07074777B2

Reaction notes

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