Triphenylphosphine → HCID 118114178, compound

HRID 2284856Notes

Reaction equation

HRID 2284856 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH:23]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:24]1[CH:40]=[CH:39][C:27]([O:28][CH2:29][C:30]2[O:34][C:33]([C:35]([O:37][CH3:38])=[O:36])=[CH:32][CH:31]=2)=[CH:26][CH:25]=1)=[N+]=[N-]>C1COCC1.O>[NH2:20][CH:23]([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:24]1[CH:40]=[CH:39][C:27]([O:28][CH2:29][C:30]2[O:34][C:33]([C:35]([O:37][CH3:38])=[O:36])=[CH:32][CH:31]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 11776Triphenylphosphine2×HCID 118114292HCID 118114292, compound

Product 1

HCID 118114178HCID 118114178, compoundYield 110.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a suspension of triphenylphosphine polymer supported (633 mg, 0.89 mmol) in THF (3 mL) was added a solution of methyl 5-((4-(azido(phenyl)methyl)phenoxy)-methyl)furan-2-carboxylate (293 mg, 0.81 mmol) in THF (6.1 mL) and H2O (0.12 mL). The reaction was stirred very slowly and heated at 60° C. for 18 h. Triphenylphosphine polymer supported (300 mg) and water (62 μL) were added and the heating was maintained at 60° C. for 5 h. The reaction was then allowed to cool to room temperature. The resin was removed by filtration, washed twice with THF and DCM. The combined organic phases were dried over MgSO4, filtered and the solvent removed in vacuo to give the title compound (301 mg) which was taken on to the next step without further purification.

Workup

  1. additionwere added
  2. temperaturethe heating was maintained at 60° C. for 5 h
  3. temperatureto cool to room temperature
  4. customThe resin was removed by filtration
  5. washwashed twice with THF and DCM
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-bab23cbe8d4e42caa5e75ca1bf5cceff
Source dataset
uspto-grants-2015_09
Patent number
US09145409B2

Reaction notes

Loading…