Potassium bisulfate → (4S)-4-benzyl-3-(5-phenylpentanoyl)-1,3-oxazolidin-2-one

HRID 59693

Reaction equation

HRID 59693 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.C([Li])CCC.[C:19]1([CH2:25][CH2:26][CH2:27][CH2:28][C:29](Cl)=[O:30])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.OS([O-])(=O)=O.[K+]>C1COCC1>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:29](=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 516920Potassium bisulfateHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 109654605-phenylpentanoyl ChlorideHCID 178418339Butyllithium

Product 1

HCID 10783156(4S)-4-benzyl-3-(5-phenylpentanoyl)-1,3-oxazolidin-2-oneYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirring solution consisting of (S)-4-benzyloxazolidin-2-one (0.9 g, 5.08 mmol) in THF (20 mL) at −78° C. was slowly added n-butyllithium solution (3.5 mL, 5.6 mmol, 1.6 M solution in hexane). The reaction mixture was stirred at −78° C. for two hours, after which time 5-phenylpentanoyl chloride (1 g, 5 mmol, prepared by treatment of 5-phenylpentanoic acid with oxalyl chloride and catalytic DMF) was slowly added. The reaction mixture was stirred at −78° C. for two hours and was then allowed to rise to room temperature overnight. The reaction mixture was acidified with 5% KHSO4 and extracted twice with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, filtered, and concentrated under vacuum. The residue was purified by silica gel chromatography. Elution with ethyl acetate-heptane (25:75 v/v) afforded the title compound (1.4 g, 82%) as a clear oil; TLC Rf 0.40 (solvent system: 25:75 v/v ethyl acetate-heptane); MS (ESI+) m/z 337.4 (M+H)+, 360.2 (M+Na)+.

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for two hours
  2. waitto rise to room temperature overnight
  3. extractionextracted twice with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by silica gel chromatography
  9. washElution with ethyl acetate-heptane (25:75 v/v)

Sources & evidence

ORD record
ord-8c0a011ccf214c169e2ed2ad5abd4a0c
Source dataset
uspto-grants-2016_09
Patent number
US09440919B2

Linked notes

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