N,N-Dimethylacrylamide → HCID 67301504, compound

HRID 1014968Notes

Reaction equation

HRID 1014968 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@:28]2([CH3:29])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:30])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@@H:21]([OH:23])[CH3:22])[CH2:12][C@@H:11]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[CH3:41][N:42]([CH3:47])[C:43](=[O:46])[CH:44]=[CH2:45].[Cl-].[NH4+]>O1CCCC1>[Si:1]([O:8][C@@H:9]1[C@@:28]2([CH3:29])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:30])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@@H:21]([O:23][CH2:45][CH2:44][C:43]([N:42]([CH3:47])[CH3:41])=[O:46])[CH3:22])[CH2:12][C@@H:11]([O:31][Si:32]([C:35]([CH3:37])([CH3:36])[CH3:38])([CH3:33])[CH3:34])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 17587N,N-DimethylacrylamideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 120200781alpha,3beta-bis(tert-butyldimethylsilyloxy)-20(S)-hydroxypregna-5,7,16-triene

Product 1

HCID 67301504HCID 67301504, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1α,3β-bis(tert-butyldimethylsilyloxy) -20(S)-hydroxypregna-5,7,16-triene (400 mg, 0.72 mmol) in tetrahydrofuran (7.2 ml), sodium hydride (60% in oil, 46 mg, 1.15 mmol) was added and stirred at room temperature for 30 minutes under a nitrogen stream. After addition of N,N-dimethylacrylamide (308 mg, 3.11 mmol), the reaction mixture was further stirred at the same temperature for 3 hours, poured into saturated aqueous ammonium chloride, extracted with ethyl acetate (3 times) and washed with saturated aqueous sodium chloride and water. The organic layer was dried over anhydrous magnesium sulfate. After evaporation under reduced pressure to remove the solvent, the resulting residue was purified by column chromatography (hexane:ethyl acetate=2:1) to give the titled compound (459 mg, 96.9%) as a colorless oil.

Workup

  1. stirringthe reaction mixture was further stirred at the same temperature for 3 hours
  2. extractionextracted with ethyl acetate (3 times)
  3. washwashed with saturated aqueous sodium chloride and water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customAfter evaporation under reduced pressure
  6. customto remove the solvent
  7. customthe resulting residue was purified by column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-1808d24e496f4458be85958728d90219
Source dataset
uspto-grants-2011_07
Patent number
US07985744B2

Reaction notes

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