Triethylamine → HCID 22262241, compound

HRID 1610765Notes

Reaction equation

HRID 1610765 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8](O)[CH:9]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]3[O:23][CH2:22][C:21]([CH3:25])([CH3:24])[C:20]=3[CH:26]=2)C(OCC)=O)[CH:5]=[CH:6][CH:7]=1.[OH-:28].[Na+].C([N:32]([CH2:35]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:44])C=CC=CC=1>O1CCCC1CCO.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:28][C:35](=[O:44])[NH:32][CH:9]2[CH2:15][C:16]2[CH:17]=[CH:18][C:19]3[O:23][CH2:22][C:21]([CH3:24])([CH3:25])[C:20]=3[CH:26]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 199401P,P-Diphenylphosphinic azideHCID 86593314HCID 86593314, compound

Product 1

HCID 22262241HCID 22262241, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 119895722-(Oxolan-2-yl)ethan-1-olSolvent

Procedure

To a solution of ethyl (2RS,3RS)-3-(3-chlorophenyl)-2-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl)methyl]-3-hydroxypropionate (11.44 g, 29.4 mmol) in tetrahydrofuran-ethanol (60 ml-60 ml) was added 1N sodium hydroxide (60 ml, 60 mmol) at room temperature, and the mixture was stirred overnight at room temperature. After completion of the reaction, the organic solvent was evaporated under reduced pressure. The aqueous layer was acidified with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered, and concentrated under reduced pressure to give a colorless transparent oil. To a solution of the oil in tetrahydrofuran (300 ml) were added triethylamine (6.2 ml, 44.1 mmol) and diphenylphosphoryl azide (7.6 ml, 35.3 mmol), and the mixture was heated under reflux for 4 hrs. The solvent was evaporated, and the residue was diluted with ethyl acetate and washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from hexane-ethyl acetate to give (4RS,5SR)-5-(3-chlorophenyl)-4-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl)methyl]-1,3-oxazolidin-2-one (8.11 g, 77%) as colorless crystals.

Workup

  1. customAfter completion of the reaction
  2. customthe organic solvent was evaporated under reduced pressure
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a colorless transparent oil
  8. temperaturethe mixture was heated
  9. temperatureunder reflux for 4 hrs
  10. customThe solvent was evaporated
  11. additionthe residue was diluted with ethyl acetate
  12. washwashed with water, saturated aqueous sodium hydrogen carbonate and saturated brine
  13. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated under reduced pressure
  16. customThe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-9ebd87a86185440588683274c082466c
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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