Triethylamine → HCID 86709391, compound

HRID 2172246Notes

Reaction equation

HRID 2172246 reaction equation
C([N:3]([CH2:6]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:15])C=CC=CC=1.[CH3:25][C:26]([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:41][CH:40]=2)=[CH:33][CH:32]=1)([CH3:30])C(O)=O>O1CCOCC1>[N:3]([C:26]([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]2[CH:40]=[CH:41][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:43][CH:44]=2)=[CH:33][CH:32]=1)([CH3:30])[CH3:25])=[C:6]=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 70873698HCID 70873698, compound

Product 1

HCID 86709391HCID 86709391, compoundYield 190.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Triethylamine (2.90 ml, 20.8 mmol) and diphenylphosphorylazide (4.48 ml, 20.8 mmol) were added to a 1,4-dioxane solution (70 ml) of 2-methyl-2-[4-(4-trifluoromethylbenzyloxy)phenyl]propionic acid (7.03 g, 10.8 mmol) and heated at reflux. After 2 hours, the solvent was distilled off, and diethylether and water were added to the residue, followed by extraction with diethylether. The result was washed with water and a saturated sodium chloride aqueous solution and dried over sodium sulfate. After removing the desiccant by filtration, the solvent was distilled off to afford the title compound as a pale brown oil (6.89 g, 99%).

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. distillationthe solvent was distilled off
  4. additiondiethylether and water were added to the residue
  5. extractionfollowed by extraction with diethylether
  6. washThe result was washed with water
  7. dry with materiala saturated sodium chloride aqueous solution and dried over sodium sulfate
  8. customAfter removing the
  9. filtrationdesiccant by filtration
  10. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-46bde07a56594fc883f23041c347d69b
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

Loading…