Pivaloyl chloride → (4S)-4-benzyl-3-(2-isopropoxyacetyl)oxazolidin-2-one

HRID 1985384

Reaction equation

HRID 1985384 reaction equation
[CH:1]([O:4][CH2:5][C:6]([OH:8])=O)([CH3:3])[CH3:2].CC(C)(C)C(Cl)=O.[Cl-].[Li+].[CH2:18]([C@H:25]1[CH2:29][O:28][C:27](=[O:30])[NH:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCCC1.C(N(CC)CC)C>[CH2:18]([C@H:25]1[CH2:29][O:28][C:27](=[O:30])[N:26]1[C:6](=[O:8])[CH2:5][O:4][CH:1]([CH3:2])[CH3:3])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 62493Pivaloyl chlorideHCID 433294Lithium ChlorideHCID 5172132-(Propan-2-yloxy)acetic acidHCID 736225(S)-4-Benzyl-2-oxazolidinone

Product 1

HCID 59997951(4S)-4-benzyl-3-(2-isopropoxyacetyl)oxazolidin-2-oneYield 56.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
-25 °C

Procedure

A solution containing 98 g of 2-isopropoxyacetic acid and 360 ml of triethylamine in tetrahydrofuran (4L) was cooled to −25° C. After 92 ml of 2,2-dimethylpropanoyl chloride was dropwise added, the reaction solution was stirred at −20° C. for 5 hours. Then, 50 g of anhydrous lithium chloride and 120 g of (4S)-4-benzyl-1,3-oxazolidin-2-one were successively added, and stirring was continued at room temperature overnight. Then, the reaction solution was filtered and evaporated. The residue was dissolved in 2 L of ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate), to give 106.6 g of (4S)-4-benzyl-3-(2-isopropoxyacetyl)-1,3-oxazolidin-2-one as a colorless oil.

Workup

  1. stirringstirring
  2. waitwas continued at room temperature overnight
  3. filtrationThen, the reaction solution was filtered
  4. customevaporated
  5. dissolutionThe residue was dissolved in 2 L of ethyl acetate
  6. washwashed with saturated aqueous sodium hydrogen carbonate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-5178ef5a9d284d738f013980ea07e27d
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Linked notes

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