Water → HCID 67461305, compound

HRID 553394Notes

Reaction equation

HRID 553394 reaction equation
[C:1]1([CH:7]2[O:12][C:11](=[O:13])[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[NH:21][S:22]([C:25]([F:28])([F:27])[F:26])(=[O:24])=[O:23])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])O.[Na+].Cl[CH2:35][O:36][CH2:37][CH3:38].O>C(#N)C>[C:1]1([CH:7]2[O:12][C:11](=[O:13])[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:21]([CH2:35][O:36][CH2:37][CH3:38])[S:22]([C:25]([F:26])([F:27])[F:28])(=[O:23])=[O:24])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 18523Chloromethyl ethyl etherHCID 516892Sodium BicarbonateHCID 67461582HCID 67461582, compound

Product 1

HCID 67461305HCID 67461305, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-Phenyl-3-[2-(trifluoromethanesulfonylamino)benzyl]-[1,3]-oxazinan-2-one (0.20 g, 0.48 mmol) and sodium hydrogen carbonate (0.08 g, 0.85 mmol) were suspended in acetonitrile (10 ml), added with chloromethylethyl ether (0.07 g, 0.83 mmol) and heated to reflux for three hours. After cooling to room temperature, the reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with a saturated brine and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 6-phenyl-3-{2-[N-(ethoxymethyl)-N-(trifluoromethanesulfonyl)amino]benzyl)-[1,3]-oxazinan-2-one (0.17 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for three hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-6a591d6f340e4e21bc09be299994c383
Source dataset
uspto-grants-2011_11
Patent number
US08048825B2

Reaction notes

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