Sodium hydride → HCID 67901865, compound

HRID 232205Notes

Reaction equation

HRID 232205 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[CH2:15][O:14][NH:13][C:12]2=[O:16])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[C:20]1([C:26]([O:28][CH3:29])=[O:27])[CH:24]=[CH:23][C:22](=[O:25])[O:21]1>CN(C)C=O.C(OCC)(=O)C.O>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[CH2:15][O:14][N:13]([C:20]3([C:26]([O:28][CH3:29])=[O:27])[CH:24]=[CH:23][C:22](=[O:25])[O:21]3)[C:12]2=[O:16])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 20030909HCID 20030909, compoundHCID 54136951HCID 54136951, compound

Product 1

HCID 67901865HCID 67901865, compoundYield 8.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

In 3 ml of anhydrous N,N-dimethylformamide was dissolved 220 mg of (4R)-4-phenylacetamido-3-isoxazolidinone. To the solution were added, under ice-cooling and stirring, 60 mg of sodium hydride (50% mineral oil) and 0.5 ml of anhydrous N,N-dimethylformamide solution dissolving 220 mg of the Compound (26) obtained in Example 26. The reaction solution was stirred for 69 minutes under ice-cooling, which was then poured into a mixture of ethyl acetate and water. The ethyl acetate layer was taken, washed with water and dried (Na2SO4). The solvent was evaporated off, and the residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (2:1→2:3) to give 32 mg of the subject Compound (30) as colorless oil.

Workup

  1. additionTo the solution were added, under ice-
  2. temperaturecooling
  3. stirringThe reaction solution was stirred for 69 minutes under ice-
  4. temperaturecooling
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was evaporated off
  8. washfollowed by elution with hexane-ethyl acetate (2:1→2:3)

Sources & evidence

ORD record
ord-df1a9465fe06425184ada2001240f48f
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Reaction notes

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