Water → HCID 86638036, compound

HRID 553400Notes

Reaction equation

HRID 553400 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:7][O:6][C:5](=[S:8])[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])[CH2:3]1.C(=O)([O-])O.[Na+].Cl[C:31]([O:33][CH3:34])=[O:32].O>C(#N)C>[CH3:1][C:2]1([CH3:24])[CH2:7][O:6][C:5](=[S:8])[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:16]([C:31]([O:33][CH3:34])=[O:32])[S:17]([C:20]([F:23])([F:21])[F:22])(=[O:19])=[O:18])[CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 86638035HCID 86638035, compound

Product 1

HCID 86638036HCID 86638036, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5,5-dimethyl-3-[2-(trifluoromethanesulfonylamino)benzyl]-[1,3]-oxazinan-2-thione (0.15 g, 0.39 mmol) and sodium hydrogen carbonate (0.05 g, 0.60 mmol) were suspended in acetonitrile (10 ml), added with methyl chloroformate (0.06 g, 0.60 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 solvent was evaporated under reduced pressure after the organic layer was dried over anhydrous sodium sulfate. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:l) to obtain 5,5-dimethyl-3-(2-[N-(methoxycarbonyl)-N-(trifluoromethanesulfonyl)amino]benzyl)-[1,3]-oxazinane-2-thione (0.08 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for three hours
  3. extractionextracted with ethyl acetate
  4. customThe solvent was evaporated under reduced pressure after the organic layer
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:l)

Sources & evidence

ORD record
ord-f56d5d2f9d8843288784dd1d04b11e28
Source dataset
uspto-grants-2011_11
Patent number
US08048825B2

Reaction notes

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