Methyl Acrylate → 3-[2-(tert-Butoxycarbonylamino-methyl)-phenyl]-acrylic acid methyl ester

HRID 1371521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1371521
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1Br)([CH3:4])([CH3:3])[CH3:2].[C:17]([O:21][CH3:22])(=[O:20])[CH:18]=[CH2:19]>CN(C=O)C.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:22][O:21][C:17](=[O:20])[CH:18]=[CH:19][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:16]

Komponenten

6

Edukt 2

HCID 7294Methyl AcrylateHCID 70183002-Bromo-N-(tert-butoxycarbonyl)benzylamine

Produkt 1

HCID 692195883-[2-(tert-Butoxycarbonylamino-methyl)-phenyl]-acrylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To compound of Step A (161.0 g, 561.8 mmol) in DMF (800 mL) is added methyl acrylate (58.0 g, 674.2 mmol), TEA (170.5 g, 1685.4 mmol) and dichlorobis(triphenylphosphine)palladium(II) (7.9 g, 11.2 mmol). The mixture is heated at 80° C. for about 32 hours. The mixture is cooled, diluted with 1000 mL of EtOAc and washed with 10% aqueous sodium bisulfate. The aqueous portion is extracted three times with EtOAc and the combined organics are dried (Na2SO4) and concentrated to dryness. The residue is dissolved in a small amount of DCM and filtered through 7 inch of silica gel in a 2 L sintered glass funnel eluting with 25% EtOAc/hexanes. The eluent is concentrated to dryness and recrystallized from EtOAc/hexanes to afford about 116.9 g (71%) of Step B compound.

Aufarbeitung

  1. temperatureThe mixture is cooled
  2. washwashed with 10% aqueous sodium bisulfate
  3. extractionThe aqueous portion is extracted three times with EtOAc
  4. dry with materialthe combined organics are dried (Na2SO4)
  5. concentrationconcentrated to dryness
  6. dissolutionThe residue is dissolved in a small amount of DCM
  7. filtrationfiltered through 7 inch of silica gel in a 2 L sintered glass funnel
  8. washeluting with 25% EtOAc/hexanes
  9. concentrationThe eluent is concentrated to dryness
  10. customrecrystallized from EtOAc/hexanes
  11. customto afford about 116.9 g (71%) of Step B compound

Quellen und Nachweise

ORD-Eintrag
ord-8afd36daa8f14f39b41258846cf77805
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157463B2

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