Water → HCID 22262221, compound

HRID 1610561Notes

Reaction equation

HRID 1610561 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([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])[N:15]=2)C(O)=O)=[CH:4][CH:3]=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]=[CH:4][C:5]([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])[N:15]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261577HCID 22261577, compound

Product 1

HCID 22262221HCID 22262221, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-{[6-(1,1,2,2-tetrafluoroethoxy)pyridin-2-yl]methyl}propanoic acid (1.20 g, 3.07 mmol) in tetrahydrofuran (20 ml) were added diphenylphosphoryl azide (730 μl, 3.37 mmol) and triethylamine (706 μl, 5.06 mmol), and the mixture was heated under reflux for 4 hrs. The reaction solution was allowed to cool and water (100 ml) was added. The mixture was extracted with ethyl acetate (50 ml×2). The extract was washed successively with saturated aqueous sodium hydrogen carbonate, water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1-1:1) to give the objective substance (808 mg, 68%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. temperatureto cool
  4. extractionThe mixture was extracted with ethyl acetate (50 ml×2)
  5. washThe extract was washed successively with saturated aqueous sodium hydrogen carbonate, water and saturated brine
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1-1:1)
  9. customto give the objective substance (808 mg, 68%)

Sources & evidence

ORD record
ord-284d78c4ef154522bd775fde223d3d86
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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