Cesium carbonate → HCID 67902274, compound

HRID 232201Notes

Reaction equation

HRID 232201 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:16][O:15][NH:14][C:13]1=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:25]1([C:31]([O:33][CH3:34])=[O:32])[CH2:29][CH2:28][C:27](=[O:30])[O:26]1>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:16][O:15][N:14]([C:25]2([C:31]([O:33][CH3:34])=[O:32])[CH2:29][CH2:28][C:27](=[O:30])[O:26]2)[C:13]1=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 14181639HCID 14181639, compoundHCID 14798665HCID 14798665, compound

Product 1

HCID 67902274HCID 67902274, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 3 ml of N,N-dimethylformamide was dissolved 236 mg of (4R)-4-benzyloxycarbonylamino-3-isoxazolidinone. To the solution was added 326 mg of cesium carbonate. The mixture was stirred at room temperature for 20 minutes, to which was added 179 mg of the Compound (13) obtained in Example 13, followed by stirring for two hours. To the reaction solution was added a dilute saline solution. The mixture was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated saline solution, which was dried (Na2SO4), then the solvent was evaporated off. The residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (1:1) to give 101 mg of the subject Compound (12). The IR and NMR spectra of this product were in complete agreement with those of the Compound (12) obtained in Example 12.

Workup

  1. stirringby stirring for two hours
  2. additionTo the reaction solution was added a dilute saline solution
  3. extractionThe mixture was subjected to extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated saline solution, which
  5. dry with materialwas dried (Na2SO4)
  6. customthe solvent was evaporated off
  7. washfollowed by elution with hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-28141c9af186413d8afb5d17288d960e
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Reaction notes

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