(S)-4-Benzyl-2-oxazolidinone → (4S)-4-benzyl-3-(5-cyclohexylpentanoyl)-1,3-oxazolidin-2-one

HRID 1279806Notes

Reaction equation

HRID 1279806 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.[CH:19]1([CH2:25][CH2:26][CH2:27][CH2:28][C:29](Cl)=[O:30])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>O1CCCC1>[CH2:6]([C@H:13]1[CH2:17][O:16][C:15](=[O:18])[N:14]1[C:29](=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 152333055-Cyclohexylpentanoyl chlorideHCID 178418339Butyllithium

Product 1

HCID 10269000(4S)-4-benzyl-3-(5-cyclohexylpentanoyl)-1,3-oxazolidin-2-oneYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of n-butyllithium (100 ml, 250 mmol, 2.5M in hexanes) was added via a cannula to a solution of (4S)-4-benzyl-1,3-oxazolidin-2-one (44.30 g, 250 mmol) in anhydrous tetrahydrofuran (400 ml) at −78° C. The yellow solution was then stirred for 45 minutes. A solution of 5-cyclohexylpentanoyl chloride (55.5 g, 275 mmol) in tetrahydrofuran (100 ml) was then added over 1 hour. The mixture was stirred at −78° C. for 30 minutes then warmed to room temperature over 1 hour. The mixture was quenched with an aqueous solution of ammonium chloride (20% w/v, 400 ml) and extracted with ethyl acetate. The layers were separated and the organic layer was washed with brine, dried over anhydrous sodium sulphate and the solvent removed under reduced pressure. The solid was recrystallised from hexane (500 ml) to afford the title compound as a white solid (81.0 g).

Workup

  1. stirringThe mixture was stirred at −78° C. for 30 minutes
  2. customThe mixture was quenched with an aqueous solution of ammonium chloride (20% w/v, 400 ml)
  3. extractionextracted with ethyl acetate
  4. customThe layers were separated
  5. washthe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. customthe solvent removed under reduced pressure
  8. customThe solid was recrystallised from hexane (500 ml)

Sources & evidence

ORD record
ord-740380e8cc34474b9c9e6822e94c83d2
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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