Water → HCID 67460004, compound

HRID 553397Notes

Reaction equation

HRID 553397 reaction equation
[CH3:1][CH:2]1[CH2:8][O:7][C:6](=[O:9])[N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH:17][S:18]([C:21]([F:24])([F:23])[F:22])(=[O:20])=[O:19])[CH2:4][CH2:3]1.C(=O)([O-])O.[Na+].Cl[C:31]([O:33][CH2:34][CH:35]([CH3:37])[CH3:36])=[O:32].O>C(#N)C>[CH2:34]([O:33][C:31]([N:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][N:5]1[CH2:4][CH2:3][CH:2]([CH3:1])[CH2:8][O:7][C:6]1=[O:9])[S:18]([C:21]([F:24])([F:22])[F:23])(=[O:20])=[O:19])=[O:32])[CH:35]([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 962WaterHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 67459000HCID 67459000, compound

Product 1

HCID 67460004HCID 67460004, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-Methyl-3-[2-(trifluoromethanesulfonylamino)benzyl]-[1,3]-oxazepan-2-one (0.15 g, 0.41 mmol) and sodium hydrogen carbonate (0.06 g, 0.71 mmol) were suspended in acetonitrile (10 ml), added with isobutyl chloroformate (00.10 g, 0.73 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 ethyl acetate 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=3:1) to obtain 3-(2-[N-(isobutoxycarbonyl)-N-(trifluoromethanesulfonyl)amino]benzyl)-6-methyl-[1,3]-oxazepan-2-one (0.10 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for three hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate 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=3:1)

Sources & evidence

ORD record
ord-51b02a80df184ba9b1c89bf6e17b6fef
Source dataset
uspto-grants-2011_11
Patent number
US08048825B2

Reaction notes

Loading…