Decanoyl chloride → 2-Oxazolidinone, 3-(1-oxodecyl)-4-(phenylmethyl)-, (4S)-

HRID 1379605Notes

Reaction equation

HRID 1379605 reaction equation
C([Li])CCC.[CH2:6]([C@H:13]1[CH2:17][O:16][C:15](=[O:18])[NH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:19](Cl)(=[O:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>C1COCC1>[O:29]=[C:19]([N:14]1[C@@H:13]([CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:17][O:16][C:15]1=[O:18])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 66982Decanoyl chlorideHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 178418339Butyllithium

Product 1

HCID 104967372-Oxazolidinone, 3-(1-oxodecyl)-4-(phenylmethyl)-, (4S)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

n-Butyl lithium (160 mL, 398 mmol, 2.5M in hexanes) is added to a solution of (S)-4-benzyl-2-oxazolidinone 51 (64 g, 362 mmol) in THF (750 mL) at -78° C. under argon and stirred for 15 min. Decanoyl chloride 59 (69 g, 362 mmol) is added to the solution dropwise and stirred for 40 min, then warmed to 0° C. for 2 hours. The reaction is quenched with NH4Cl and extracted with EtOAc. The organic layer is washed with 1N HCl, aqueous NaHCO3, aqueous NaCl, and dried over MgSO4. The crude product is recrystallized from hexane to give 60.

Workup

  1. stirringstirred for 40 min
  2. customThe reaction is quenched with NH4Cl
  3. extractionextracted with EtOAc
  4. washThe organic layer is washed with 1N HCl, aqueous NaHCO3, aqueous NaCl
  5. dry with materialdried over MgSO4
  6. customThe crude product is recrystallized from hexane

Sources & evidence

ORD record
ord-c46997f1cf554944b3ad7ae6b23d00bb
Source dataset
uspto-grants-1997_09
Patent number
US05672598

Reaction notes

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