Water → HCID 23150978, compound

HRID 1984703Notes

Reaction equation

HRID 1984703 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]1[CH:16]=[C:15]([CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH:14]=[CH:13][N:12]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:26]I.O>CCCCCC.CN(C)C=O>[C:3]([O:7][C:8]([N:10]([C:11]1[CH:16]=[C:15]([CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:20])[CH3:21])[CH:14]=[CH:13][N:12]=1)[CH3:26])=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23151134HCID 23151134, compound

Product 1

HCID 23150978HCID 23150978, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

60% Sodium hydride (310 mg, 7.6 mmol) was washed with hexane (5.0 mL), and the residue was suspended in N,N-dimethylformamide (20 mL). 2-tert-Butoxycarbonylamino-4-(tert-butyldimethylsilyloxymethyl)pyridine (Reference compound No. 5-1, 1.3 g, 3.7 mmol) was added dropwise to the suspension for 15 minutes under ice-cooling, and methyl iodide (2.4 mL, 39 mmol) was added thereto, and then the mixture was stirred overnight at room temperature. Water (70 mL) was added to the reaction suspension, and the whole was extracted with ethyl acetate (100 mL). The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (50 mL) and brine (100 mL), and dried over anhydrous magnesium sulfate. The organic layer was evaporated under reduced pressure to give 1.4 g of the mixture including the title reference compound as an orange-red oil.

Workup

  1. addition5-1, 1.3 g, 3.7 mmol) was added dropwise to the suspension for 15 minutes under ice-
  2. temperaturecooling
  3. extractionthe whole was extracted with ethyl acetate (100 mL)
  4. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (50 mL) and brine (100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe organic layer was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ec99a7de30884897a150b7806f145ce7
Source dataset
uspto-grants-2009_06
Patent number
US07544703B2

Reaction notes

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