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Water → 3-{2-[N-(propoxycarbonyl)-N-(trifluoromethanesulfonyl)amino]benzyl)-[1,3]-oxazinan-2-one

HRID 553391
Notes
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Reaction equation

HRID 553391 reaction equation
[F:1][C:2]([F:22])([F:21])[S:3]([NH:6][C:7]1[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=1[CH2:9][N:10]1[CH2:15][CH2:14][CH2:13][O:12][C:11]1=[O:16])(=[O:5])=[O:4].C(=O)([O-])O.[Na+].Cl[C:29]([O:31][CH2:32][CH2:33][CH3:34])=[O:30].O>C(#N)C>[CH2:32]([O:31][C:29]([N:6]([C:7]1[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=1[CH2:9][N:10]1[CH2:15][CH2:14][CH2:13][O:12][C:11]1=[O:16])[S:3]([C:2]([F:1])([F:21])[F:22])(=[O:5])=[O:4])=[O:30])[CH2:33][CH3:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 7998Propyl chloroformateHCID 516892Sodium BicarbonateHCID 509434753-[2-(Trifluoromethanesulfonylamino)benzyl]-[1,3]-oxazinan-2-one

Product 1

HCID 674589973-{2-[N-(propoxycarbonyl)-N-(trifluoromethanesulfonyl)amino]benzyl)-[1,3]-oxazinan-2-oneYield 68.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-[2-(Trifluoromethanesulfonylamino)benzyl]-[1,3]-oxazinan-2-one (0.13 g, 0.38 mmol) and sodium hydrogen carbonate (0.06 g, 0.71 mmol) was suspended in acetonitrile (15 ml), added with propyl chloroformate (0.09 g, 0.77 mmol) and heated to reflux for six 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=1:4) to obtain 3-{2-[N-(propoxycarbonyl)-N-(trifluoromethanesulfonyl)amino]benzyl)-[1,3]-oxazinan-2-one (0.11 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for six 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=1:4)

Sources & evidence

ORD record
ord-6b8d7d689bc74860aaa9e3e40448eaac
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08048825B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes