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

HRID 409341Notes

Reaction equation

HRID 409341 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-c7cbc2b3080a4eb9b02091749792644b
Source dataset
uspto-grants-2014_06
Patent number
US08759380B2

Reaction notes

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