Di-tert-butyl dicarbonate → Methyl 4-[2-dimethylaminoethyl-[tert-butoxycarbonyl]amino]benzoate

HRID 16752Notes

Reaction equation

HRID 16752 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][NH:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1.C(=O)(OC(C)(C)C)[O:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=O>C1COCC1>[CH3:16][N:2]([CH3:1])[CH2:3][CH2:4][N:5]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:18])[C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 57440398Methyl 4-{[2-(dimethylamino)ethyl]amino}benzoate

Product 1

HCID 57440397Methyl 4-[2-dimethylaminoethyl-[tert-butoxycarbonyl]amino]benzoateYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-(2-[dimethylamino]ethylamino)benzoate (1.00 g, 4.50 mmol) was dissolved in THF (30 ml). (2-Methylpropan-2-yl)oxycarbonyl tert-butyl carbonate (1.035 g, 4.72 mmol) was added and the solution was refluxed for 3 h. The solvent was then evaporated, the residue was dissolved in DCM, washed with sat. aq. ammonium chloride solution, dried over sodium sulphate, filtered and evaporated to give methyl 4-[2-dimethylaminoethyl-[tert-butoxycarbonyl]amino]benzoate (1.07 g, 74%) as a brown oil.

Workup

  1. temperaturethe solution was refluxed for 3 h
  2. customThe solvent was then evaporated
  3. dissolutionthe residue was dissolved in DCM
  4. washwashed with sat. aq. ammonium chloride solution
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-2c0cfb95e1d6413693d85586c897af9e
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Reaction notes

Loading…