Water → HCID 22262167, compound

HRID 1610283Notes

Reaction equation

HRID 1610283 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:21])[CH:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[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:41]([CH2:44]C)CC)C.[OH2:46]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[O:21][C:44](=[O:46])[NH:41][CH:9]2[CH2:13][C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261633HCID 22261633, compound

Product 1

HCID 22262167HCID 22262167, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS,3RS)-3-(4-fluorophenyl)-2-(4-fluorobenzyl)-3-hydroxypropionic acid (13.8 g, 47.2 mmol) in tetrahydrofuran (150 ml) were added diphenylphosphoryl azide (13.2 ml, 61.4 mmol) and triethylamine (9.2 ml, 66.1 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 (200 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, passed through a small amount of silica gel and evaporated under reduced pressure. The residue was crystallized from hexane-ethyl acetate to give (4RS,5SR)-5-(4-fluorophenyl)-4-((4-fluorophenyl)methyl)-1,3-oxazolidin-2-one (12.8 g, 94%) 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 crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-4109d070bc804f00aa2b7b6aef7dac29
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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