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

HRID 2305230Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2305230
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]

Komponenten

7

Edukt 5

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 167845palladium(II) acetateKatalysator

Reaktionsbedingungen

Temperatur
78 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-c9eea0ea7072494e89b772851a645535
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06437146B1

Notizen zur Reaktion

Wird geladen…