Triphenylphosphine → t-Butyloxycarbonylamino-3-[2-(4-cyanophenyl)ethoxy]benzene

HRID 325025

Reaction equation

HRID 325025 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:35]([C:37]1[CH:42]=[CH:41][C:40]([CH2:43][CH2:44]O)=[CH:39][CH:38]=1)#[N:36].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:44][CH2:43][C:40]2[CH:41]=[CH:42][C:37]([C:35]#[N:36])=[CH:38][CH:39]=2)[CH:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 312485tert-butyl N-(3-hydroxyphenyl)carbamateHCID 28008154-(2-Hydroxyethyl)benzonitrileHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 22033522t-Butyloxycarbonylamino-3-[2-(4-cyanophenyl)ethoxy]benzeneYield 44.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of t-butyloxycarbonylamino-3-hydroxybenzene (418.5 mg; 2 mmol; from step (i) above), triphenylphosphine (629.5 mg; 2.4 mmol) and 2-(4-cyanophenyl)ethanol (353.2 mg; 2.4 mmol) in THF (50 mL), under an atmosphere of nitrogen, was added diethylazodicarboxylate (518 mg; 3 mmol) and the mixture was stirred for one week. Ice cold water was added and the THF was removed by evaporation. The remaining water phase was extracted three times with EtOAc. The combined organic phase was washed twice with 0.2 M NaOH, once with brine, and then dried (Na2SO4). Evaporation followed by flash chromatography using a stepwise gradient of toluene:EtOAc (100:0, 90:10, 80:20 and 60:40) gave 300 mg (44%) of the sub-title compound.

Workup

  1. additionIce cold water was added
  2. customthe THF was removed by evaporation
  3. extractionThe remaining water phase was extracted three times with EtOAc
  4. washThe combined organic phase was washed twice with 0.2 M NaOH, once with brine
  5. dry with materialdried (Na2SO4)
  6. customEvaporation

Sources & evidence

ORD record
ord-e5b8a547495d4d43b883be3cf3eaf95f
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Linked notes

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