Water → HCID 23564892, compound

HRID 1059458Notes

Reaction equation

HRID 1059458 reaction equation
[O:1]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]2[S:18][C:17]3[N:19]=[CH:20][CH:21]=[N:22][C:16]=3[NH:15][C:14]=2[CH:23]=1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[H-].[Na+].[C:26](Cl)(=[O:28])[CH3:27].O>CN(C)C=O>[C:26]([N:15]1[C:14]2[CH:23]=[C:10]([CH2:9][O:1][Si:2]([C:5]([CH3:6])([CH3:7])[CH3:8])([CH3:4])[CH3:3])[CH:11]=[CH:12][C:13]=2[S:18][C:17]2[N:19]=[CH:20][CH:21]=[N:22][C:16]1=2)(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 23564737HCID 23564737, compound

Product 1

HCID 23564892HCID 23564892, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4.0 g of 8-(tert-butyldimethylsiloxymethyl)-10H-pyrazino[2,3-b][1,4]benzothiazine in 50 ml of N,N-dimethylformamide was added 0.73 g of sodium hydride (60%) and the resulting mixture was stirred for 10 minutes. After adding 1.4 ml of acetyl chloride thereto, the resulting mixture was reacted at room temperature for 10 minutes. After adding water followed by extraction with ethyl acetate, the extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluting with ethyl acetate/hexane) to thereby give 2.5 g of the title compound as a yellow oily substance.

Workup

  1. customthe resulting mixture was reacted at room temperature for 10 minutes
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe extract was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluting with ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f7d70e6097db4b1699a1660b8eae5295
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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