Water → HCID 86676907, compound

HRID 332677Notes

Reaction equation

HRID 332677 reaction equation
[N:1]([CH:4]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][CH:31]=1)[O:8][CH2:9][C:10]1[CH:28]=[CH:27][C:13]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH:20]([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23])=[O:15])=[CH:12][CH:11]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[NH2:1][CH:4]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][CH:31]=1)[O:8][CH2:9][C:10]1[CH:28]=[CH:27][C:13]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH:20]([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23])=[O:15])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86676905HCID 86676905, compound

Product 1

HCID 86676907HCID 86676907, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-((3-(azido(phenyl)methyl)phenoxy)methyl)-N-(4,4-diethoxybutyl)benzamide (0.51 g, 1.03 mmol) in tetrahydrofuran (10 mL), was added polymer supported triphenylphosphine (3 mmol/g, 0.38 g, 1.13 mmol) and water (0.2 mL). The reaction mixture was stirred at 60° C. for 16 hours. The reaction mixture was allowed to cool to room temperature, filtered, the filter-cake washed with dichloromethane and concentrated under reduced pressure to give the title compound (0.41 g, 83%).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. washthe filter-cake washed with dichloromethane
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d94280999d5f4aceb85176d21993f35d
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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