Hydrochloric Acid → 3-Oxazolidineacetic acid, 2-oxo-4,5-diphenyl-, ethyl ester, cis-

HRID 1762166Notes

Reaction equation

HRID 1762166 reaction equation
[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:10][C:9](=[O:18])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].Cl>O1CCCC1>[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[O:10][C:9](=[O:18])[N:8]2[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 9859564(4S,5R)-(-)-cis-4,5-Diphenyl-2-oxazolidinone

Product 1

HCID 674151183-Oxazolidineacetic acid, 2-oxo-4,5-diphenyl-, ethyl ester, cis-Yield 61.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,5-cis-Diphenyl-2-oxooxazolidine (48.6 g, 203 mmol) was suspended in tetrahydrofuran (330 ml) and, under ice-cooling, sodium hydride (8.12 g, 203 mmol) was added carefully. Thereafter, ethyl bromoacetate (33.9 g, 203 mmol) was added dropwise. The mixture was stirred at room temperature for 4 hours, poured into a mixture of a 10-fold dilution of conc. hydrochloric acid (60 ml) and ice-water (50 ml) and extracted twice with ethyl acetate. The extract was washed with saturated aqueous sodium chloride and dried over sodium sulfate. After filtration, the filtrate was concentrated and the residue was purified by silica gel column chromatography [eluent: n-hexane-ethyl acetate (4:1)] to give the title compound (40.6 g) as yellow oil.

Workup

  1. temperaturecooling
  2. extractionextracted twice with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. customthe residue was purified by silica gel column chromatography [eluent: n-hexane-ethyl acetate (4:1)]

Sources & evidence

ORD record
ord-09680df0338245e985edab0034e5a080
Source dataset
uspto-grants-1989_05
Patent number
US04831026

Reaction notes

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