Water → (4RS,5SR)-5-(4-fluorophenyl)-4-((4-(methyloxy)phenyl)methyl)-1,3-oxazolidin-2-one

HRID 1610291Notes

Reaction equation

HRID 1610291 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:22])[CH:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][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:42]([CH2:45]C)CC)C.[OH2:47]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[O:22][C:45](=[O:47])[NH:42][CH:9]2[CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261867(2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-(4-methoxybenzyl)propionic acid

Product 1

HCID 22261570(4RS,5SR)-5-(4-fluorophenyl)-4-((4-(methyloxy)phenyl)methyl)-1,3-oxazolidin-2-oneYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-(4-methoxybenzyl)propionic acid (13.7 g, 45.0 mmol) in tetrahydrofuran (150 ml) were added diphenylphosphoryl azide (12.6 ml, 58.5 mmol) and triethylamine (8.78 ml, 63.0 mmol) and the mixture was stirred for 30 min. The mixture was further heated under reflux for 4 hrs and allowed to stand at room temperature. Water (2.00 ml) was added and the mixture was extracted with ethyl acetate (200 ml). The extract was washed with 1N hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:ethyl acetate=4:1-2:1) to give (4RS,5SR)-5-(4-fluorophenyl)-4-((4-(methyloxy)phenyl)methyl)-1,3-oxazolidin-2-one (13.0 g, 96%) as crystals.

Workup

  1. temperatureThe mixture was further heated
  2. temperatureunder reflux for 4 hrs
  3. customto stand at room temperature
  4. extractionthe mixture was extracted with ethyl acetate (200 ml)
  5. washThe extract was washed with 1N hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform:ethyl acetate=4:1-2:1)

Sources & evidence

ORD record
ord-afd21aa41da14ac1a23144af8c5a7e5e
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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