Water → HCID 22261598, compound

HRID 1610518Notes

Reaction equation

HRID 1610518 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([OH:27])[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:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C([N:47]([CH2:50]C)CC)C.[OH2:52]>O1CCCC1>[F:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[O:27][C:50](=[O:52])[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:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 17862109HCID 17862109, compound

Product 1

HCID 22261598HCID 22261598, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS,3RS)-3-(6-fluoropyridin-3-yl)-3-hydroxy-2-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)propionic acid (3.6 g, 9.20 mmol, (2RS,3SR) form: (2RS,3RS) form=10:1) in tetrahydrofuran (90 ml) were added diphenylphosphoryl azide (2.18 ml, 10.1 mmol) and triethylamine (1.93 ml, 13.8 mmol), and the mixture was heated under reflux for 30 min. 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, saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give (4RS,5SR)-5-(6-fluoropyridin-3-yl)-4-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)-1,3-oxazolidin-2-one (3.31 g, (4RS,5SR) form: (4RS,5RS) form=10:1, 93%) as an amorphous compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 min
  3. temperatureto cool
  4. extractionThe mixture was extracted with ethyl acetate (100 ml×2)
  5. washThe extract was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-66574c48233444b6ae50ec72178b6057
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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