Ammonium Chloride → (4R)-4-Benzyl-3-(3-methylbutanoyl)-1,3-oxazolidin-2-one

HRID 393696Notes

Reaction equation

HRID 393696 reaction equation
[Li+].CCC[CH2-].[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:24])[CH2:20][CH:21]([CH3:23])[CH3:22].[Cl-].[NH4+]>O1CCCC1>[CH2:6]([C@@H:13]1[CH2:17][O:16][C:15](=[O:18])[N:14]1[C:19](=[O:24])[CH2:20][CH:21]([CH3:23])[CH3:22])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 61028n-Butyl lithiumHCID 66054Isovaleryl chlorideHCID 2734969(R)-4-Benzyl-2-oxazolidinone

Product 1

HCID 11391340(4R)-4-Benzyl-3-(3-methylbutanoyl)-1,3-oxazolidin-2-oneYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Butyllithium (2M in hexanes, 50 ml) was added to a solution of (R)-4-benzyloxazolidin-2-one (17 g) in tetrahydrofuran at −78° C. and the suspension was stirred for 30 minutes, then isovaleryl chloride (12 g) was added dropwise. The solution was stirred for 30 min, allowed to warm to room temperature, and saturated ammonium chloride (200 ml) was added. The mixture was evaporated in vacuo and extracted with diethyl ether (2×100 ml), the solvent washed with water and saturated brine, dried (Na2SO4) and evaporated to give the title compound as a colourless solid (25.0 g, 95%).

Workup

  1. stirringThe solution was stirred for 30 min
  2. customThe mixture was evaporated in vacuo
  3. extractionextracted with diethyl ether (2×100 ml)
  4. washthe solvent washed with water and saturated brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-e49655d869f14de9aa6ac34352a0f48c
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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