Hydrochloric Acid → (S)-4-Benzyl-2-oxazolidinone

HRID 484383Notes

Reaction equation

HRID 484383 reaction equation
[NH2:1][C@@H:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][OH:4].[C:12](=O)(OCC)[O:13]CC.Cl>C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>[CH2:5]([C@H:2]1[CH2:3][O:4][C:12](=[O:13])[NH:1]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 447213phenylalaninol, (S)-

Product 1

HCID 736225(S)-4-Benzyl-2-oxazolidinoneYield 100%

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (2S)-2-amino-3-phenyl-1-propanol (0.649 g; 4.29 mmol) and diethyl carbonate (1.04 ml; 8.58 mmol), anhydrous potassium carbonate (20 mg; 0.14 mmol) was added, and the mixture was stirred at 120° to 130° C. for 3 hours. After cooling, to the resulting mixture 1N hydrochloric acid (1.5 ml) and ethyl acetate (about 50 ml) were added and stirred. The organic layer was separated and washed with brine, and dried over anhydrous magnesium sulfate. Distilling off the solvent under reduced pressure gave (4S)-4-benzyloxazolidin-2-one (0.760 g, quantitative yield) as a colorless solid. The sample for analysis was obtained by recrystallization from a mixed solvent of cyclohexane and toluene (1:1). Colorless crystals. M.P., 88°-89° C.

Workup

  1. additionwas added
  2. additionwere added
  3. stirringstirred
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationDistilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-c6c0edae06dd4c489f3173c34fbc17ee
Source dataset
uspto-grants-1993_07
Patent number
US05231179

Reaction notes

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