Water → HCID 22261713, compound

HRID 1610538Notes

Reaction equation

HRID 1610538 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8](O)[CH:9]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:26])([F:25])[CH:22]([F:24])[F:23])[CH:15]=2)C(O)=O)[CH:5]=[CH:6][CH:7]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:35])C=CC=CC=1.C([N:47]([CH2:50]C)CC)C.[OH2:52]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:52][C:50](=[O:35])[NH:47][CH:9]2[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:25])([F:26])[CH:22]([F:23])[F:24])[CH:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 17862246HCID 17862246, compound

Product 1

HCID 22261713HCID 22261713, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS,3RS)-3-(3-fluorophenyl)-3-hydroxy-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoic acid (4.15 g, 10.6 mmol) in tetrahydrofuran (80 ml) were added diphenylphosphoryl azide (2.52 ml, 11.7 mmol) and triethylamine (2.23 ml, 16.0 mmol), and the mixture was heated under reflux for 3 hrs. The reaction solution was allowed to cool and water (200 ml) was added. The mixture was extracted with ethyl acetate (100 ml×2). The extract was washed successively with 1N hydrochloric acid, aqueous sodium hydrogen carbonate and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. Recrystallization of the residue from ethyl acetate-hexane gave the objective substance (3.46 g, 84%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hrs
  3. temperatureto cool
  4. extractionThe mixture was extracted with ethyl acetate (100 ml×2)
  5. washThe extract was washed successively with 1N hydrochloric acid, aqueous sodium hydrogen carbonate and saturated brine
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. customevaporated under reduced pressure
  8. customRecrystallization of the residue from ethyl acetate-hexane
  9. customgave the objective substance (3.46 g, 84%)

Sources & evidence

ORD record
ord-936a8b69f6014bff87a453441bbb2814
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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