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

HRID 1092023Notes

Reaction equation

HRID 1092023 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-cb8e09e58a5a4cc2bff4cd2a0ae92577
Source dataset
uspto-grants-2012_03
Patent number
US08129391B2

Reaction notes

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