Ammonium Chloride → (S)-4-isopropyl-3-(3-phenylpropanoyl)oxazolidin-2-one

HRID 732355Notes

Reaction equation

HRID 732355 reaction equation
C([Li])CCC.[CH:6]([C@H:9]1[CH2:13][O:12][C:11](=[O:14])[NH:10]1)([CH3:8])[CH3:7].[C:15]1([CH2:21][CH2:22][C:23](Cl)=[O:24])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>C1COCC1>[CH:6]([C@H:9]1[CH2:13][O:12][C:11](=[O:14])[N:10]1[C:23](=[O:24])[CH2:22][CH2:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 64801Benzenepropanoyl chlorideHCID 7157133(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 10467835(S)-4-isopropyl-3-(3-phenylpropanoyl)oxazolidin-2-oneYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-55 °C

Procedure

Add n-butyllithium (2.5 M solution in hexanes, 32 mL of, 80 mmol) to a solution of 4-(S)-isopropyloxazolidin-2-one (10.26 g, 79.4 mmol) in THF (250 mL) at −78° C. Stir 30 min. Add 3-phenylpropionyl chloride (13.2 mL, 89 mmol) over 4 min. Stir 2.5 h at −78° C., then warm to −55° C. and stir 2 h. Add saturated aqueous ammonium chloride (75 mL) and warm to room temperature. Extract with dichloromethane and wash extract with 1 N NaOH (200 mL), saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate. Add hexanes (50 mL), filter solids and dry under vacuum to give a white solid (18.94 g, 91%).

Workup

  1. stirringStir 2.5 h at −78° C.
  2. stirringstir 2 h
  3. extractionExtract with dichloromethane
  4. washwash
  5. extractionextract with 1 N NaOH (200 mL), saturated aqueous sodium chloride
  6. dry with materialdry (magnesium sulfate)
  7. concentrationconcentrate
  8. filtrationAdd hexanes (50 mL), filter solids
  9. customdry under vacuum

Sources & evidence

ORD record
ord-ccfefcfd7ef44058b7488fc333844d3b
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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