Methanol → Methyl 4-[2-(tert-butoxycarbonylamino)ethyl]benzoate

HRID 2305230Notes

Reaction equation

HRID 2305230 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:9][CH:8]=1)(=O)=O.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH3:61][OH:62].CN([CH:66]=[O:67])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:19]([O:18][C:16]([NH:15][CH2:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:61]([O:67][CH3:66])=[O:62])=[CH:8][CH:9]=1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 18459135trifluoro-methanesulfonic Acid 4-(2-tert-butoxycarbonylamino-ethyl)-phenyl Ester

Product 1

HCID 22710013Methyl 4-[2-(tert-butoxycarbonylamino)ethyl]benzoateYield 76%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
78 °C

Procedure

A mixture of 4-[2-(tert-butoxycarbonylamino)ethyl]-phenyl trifluoromethanesulfonate (6.11 g, 16.6 mmol), palladium(II) acetate (745 mg, 3.32 mmol), 1,3-bis-(diphenylphosphino)propane (1.37 g, 3.32 mmol), triethylamine (6.94 ml, 49.8 mmol), and MeOH (24ml) in DMF (60 ml) was purged for 30 min with carbon monoxide. The mixture was stirred under carbon monoxide atmosphere at 78° C. for 3 hours. After cooling the mixture to room temperature, the reaction mixture was diluted with EtOAc, washed with water, 1N-hydrochloric acid, water, saturated sodium hydrogencarbonate, water and brine successively, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:EtOAc, 4:1-3:1) to give methyl 4-[2-(tert-butoxycarbonylamino)ethyl]benzoate (3.52 g, 76%).

Workup

  1. customwas purged for 30 min with carbon monoxide
  2. temperatureAfter cooling the mixture to room temperature
  3. additionthe reaction mixture was diluted with EtOAc
  4. washwashed with water, 1N-hydrochloric acid, water, saturated sodium hydrogencarbonate, water and brine successively
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane:EtOAc, 4:1-3:1)

Sources & evidence

ORD record
ord-c9eea0ea7072494e89b772851a645535
Source dataset
uspto-grants-2002_08
Patent number
US06437146B1

Reaction notes

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