Acetone → Tert-butyl 4-(2-((tert-butoxycarbonyl)(methyl)amino)phenyl)-2-nitrobenzoate

HRID 454493Notes

Reaction equation

HRID 454493 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.CC(C)=O.[C:18]([O:22][C:23]([NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]1[CH:44]=[CH:43][C:35]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[C:34]([N+:45]([O-:47])=[O:46])[CH:33]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>C(OCC)(=O)C.O>[C:18]([O:22][C:23]([N:25]([CH3:1])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]1[CH:44]=[CH:43][C:35]([C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])=[C:34]([N+:45]([O-:47])=[O:46])[CH:33]=1)=[O:24])([CH3:19])([CH3:20])[CH3:21]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 66990464Tert-butyl 4-(2-(tert-butoxycarbonylamino)phenyl)-2-nitrobenzoate

Product 1

HCID 66990486Tert-butyl 4-(2-((tert-butoxycarbonyl)(methyl)amino)phenyl)-2-nitrobenzoateYield 21.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (0.16 g) and dimethyl sulfate (0.094 mL) were added to an acetone (4.0 mL) solution of tert-butyl 4-(2-(tert-butoxycarbonylamino)phenyl)-2-nitrobenzoate (0.27 g), followed by heating to reflux for 2 hours. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 95-85% hexane/ethyl acetate] and then purified by silica gel column chromatography [eluent: 91-85% hexane/ethyl acetate] to obtain 0.061 g of tert-butyl 4-(2-((tert-butoxycarbonyl)(methyl)amino)phenyl)-2-nitrobenzoate as a colorless oily substance.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 2 hours
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [eluent: 95-85% hexane/ethyl acetate]
  8. custompurified by silica gel column chromatography [eluent: 91-85% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-4c2c44e4e45d44eb849d781e39582396
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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