(S)-4-Benzyl-2-oxazolidinone → (S)-4-Benzyl-3-(2-(4-fluorophenyl)acetyl)oxazolidin-2-one

HRID 922693Notes

Reaction equation

HRID 922693 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](Cl)=[O:28])=[CH:22][CH:21]=1>C1COCC1>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:27](=[O:28])[CH2:26][C:23]1[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 37449884-Fluorophenylacetyl chlorideHCID 178418339Butyllithium

Product 1

HCID 15536019(S)-4-Benzyl-3-(2-(4-fluorophenyl)acetyl)oxazolidin-2-oneYield 8,089%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (−78° C.) solution of (S)-4-benzyloxazolidin-2-one (10.26 g, 58 mmol, 1.0 equiv) in 100 mL THF was added dropwise n-BuLi (40 mL, 1.6 M, 64 mmol, 1.1 equiv). After stirring for 30 minutes, 4-fluorophenylacetyl chloride (10.0 g, 0.58 mmol, 1.0 equiv) was added dropwise. After stirring for an additional 30 minutes, the reaction mixture was allowed to warm to room temperature. The reaction was quenched with sat'd. aq. NH4Cl, extracted with DCM, and washed with brine. The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by silica gel (10-20% EtOAc/Hexanes) provided the title compound as a thick oil (14.7 g, 81%). m/z=314.3 [M+H]+.

Workup

  1. stirringAfter stirring for an additional 30 minutes
  2. customThe reaction was quenched with sat'd
  3. extractionaq. NH4Cl, extracted with DCM
  4. washwashed with brine
  5. dry with materialThe organic layer was then dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by silica gel (10-20% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-8ed3b63bda394d9e897769c8e8154eae
Source dataset
uspto-grants-2016_03
Patent number
US09278962B2

Reaction notes

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