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

HRID 1791854Notes

Reaction equation

HRID 1791854 reaction equation
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]

Participants

4

Reactant 1

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

Product 1

HCID 22033540Amino-3-[2-(4-cyanophenyl)ethoxy]-2-methylbenzeneYield 21.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5072aaaf7af947d3ab046709fd2cf87e
Source dataset
uspto-grants-2006_07
Patent number
US07074820B2

Reaction notes

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