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

HRID 1911324Notes

Reaction equation

HRID 1911324 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-ea4de7c1d79540a0bc13f52efb1e736d
Source dataset
uspto-grants-2013_12
Patent number
US08604022B2

Reaction notes

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