Water → Methyl 4-(1-ethoxycarbonylamino-1-methylethyl)benzoate

HRID 2411191Notes

Reaction equation

HRID 2411191 reaction equation
[NH2:1][C:2]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].C(=O)([O-])O.[Na+].[C:20](Cl)(=[O:24])[O:21][CH2:22][CH3:23].O>ClCCl>[CH2:22]([O:21][C:20]([NH:1][C:2]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)([CH3:3])[CH3:4])=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 57572309Methyl 4-(1-amino-1-methylethyl)benzoate

Product 1

HCID 71252297Methyl 4-(1-ethoxycarbonylamino-1-methylethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 4-(1-amino-1-methylethyl)benzoate (410 mg) in dichloromethane (15 mL) was added saturated aqueous sodium hydrogen carbonate solution (3 mL), a solution of ethyl chlorocarbonate (0.24 mL) in dichloromethane (5 mL) was added dropwise under ice-cooling, and the mixture was stirred at the same temperature for 1 hr and at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was dried over sodium sulfate, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (551 mg).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated
  5. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-f5a07ba99c264312bd92b6ecbe1fef89
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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