t-Butoxycarbonylamino-3-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene → Amino-3-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene

HRID 1791854Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1791854
C(OC([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=2)[C:10]=1[CH3:26])=O)(C)(C)C>CCOC(C)=O.Cl>[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[CH:22][CH:23]=2)[C:10]=1[CH3:26]

Komponenten

4

Edukt 1

HCID 22033517t-Butoxycarbonylamino-3-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene

Produkt 1

HCID 22033540Amino-3-[2-(4-cyanophenyl)ethoxy]-2-methylbenzeneAusbeute 21,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

t-Butoxycarbonylamino-3-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene (2.69 g, 7.64 mmol; from step (ii) above) were dissolved in EtOAc, pre-saturated with HCl(g), (150 mL) under nitrogen and stirred at room temperature overnight. After evaporation of the solvent the residue was partitioned between 10% aqueous HCl and EtOAc. The aqueous phase was washed with EtOAc, basified with NaOH (2M, aq.) and extracted with EtOAc. The combined organic phases were washed with brine, dried (MgSO4) and the solvent evaporated to afford 0.42 g (19%) of the sub-title compound.

Aufarbeitung

  1. customAfter evaporation of the solvent the residue
  2. customwas partitioned between 10% aqueous HCl and EtOAc
  3. washThe aqueous phase was washed with EtOAc
  4. extractionextracted with EtOAc
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-5072aaaf7af947d3ab046709fd2cf87e
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074820B2

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