Hexane → HCID 10924995, compound

HRID 484382Notes

Reaction equation

HRID 484382 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.CCCCCC.[Br:25][CH:26]([CH3:30])[C:27](Br)=[O:28].C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[Br:25][CH:26]([CH3:30])[C:27]([N:9]1[C@@H:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][O:11][C:10]1=[O:13])=[O:28]

Participants

8

Reactant 5

HCID 8058HexaneHCID 79047Propanoyl bromide, 2-bromo-HCID 516892Sodium BicarbonateHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 178418339Butyllithium

Product 1

HCID 10924995HCID 10924995, compoundYield 47.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4S)-4-benzyloxazolidin-2-one (0.164 g; 0.927 mmol) in dry tetrahydrofuran (3.8 ml), a 1.62 N solution of n-butyl lithium in hexane (0.571 ml; 0.927 mmol) was added at 0° C., and then 2-bromopropionyl bromide (0.106 ml; 1.01 mmol) was added at the same temperature. After 10 minutes, an aqueous solution of saturated sodium hydrogen carbonate (1 ml) was added to decompose the excess reaction agent. The reaction mixture was diluted with ethyl acetate, washed with brine and dried over anhydrous magnesium sulfate. After distilling off the solvent, the resulting solid was purified by silica gel chromatography (hexane:dichloromethane=2:3-0:1) to give a less polar (4S)-3-(2'-bromopropionyl)-4-benzyloxazolidin-2-one (0.137 g, yield, 47%) and a (4S)-3-(2'-bromopropionyl)-4-benzyloxazolidin-2-one (0.145 g, yield, 50%).

Workup

  1. washwashed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationAfter distilling off the solvent
  4. customthe resulting solid was purified by silica gel chromatography (hexane:dichloromethane=2:3-0:1)

Sources & evidence

ORD record
ord-3374de9205e54bb1acbdb84627d79b11
Source dataset
uspto-grants-1993_07
Patent number
US05231179

Reaction notes

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