Sodium Acetate → HCID 15052068, compound

HRID 329567Notes

Reaction equation

HRID 329567 reaction equation
C([O-])(=O)C.[Na+].[Cl:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]([C:16]2[C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=[CH:18][N:17]=2)=[O:15])[CH:10]=[CH:9][C:8]=1[CH2:25][N:26]1[C:30](=[O:31])[C:29]([CH3:33])([CH3:32])[CH2:28][O:27]1>C(OC(=O)C)(=O)C>[Cl:6][C:7]1[CH:12]=[C:11]([N:13]2[C:22](=[O:24])[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[C:14]2=[O:15])[CH:10]=[CH:9][C:8]=1[CH2:25][N:26]1[C:30](=[O:31])[C:29]([CH3:33])([CH3:32])[CH2:28][O:27]1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 15052019HCID 15052019, compound

Product 1

HCID 15052068HCID 15052068, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Using a method analogous to that of M. P. Cava et al., supra, a solution of 5.0 grams (0.061 mole) of sodium acetate in 50 mL of acetic anhydride was stirred while heating with a steam bath, and 1.5 grams (0.004 mole) of 2-[[2-chloro-4-[(3-carboxy-2-pyridinyl)carbonylamino]phenyl]methyl]-4,4-dimethyl-3-isoxazolidinone was added in one portion. Upon completion of addition the reaction mixture was heated with the steam bath for an additional 30 minutes. The reaction mixture was poured into 500 mL of ice-water, and the resultant solid was collected by filtration. The solid was recrystallized from acetone-water to yield 0.45 gram of 2-[[2-chloro-4-(pyrrolo[3,4-b]pyridine-5,7-dione-6-yl)phenyl]-methyl]-4,4-dimethyl-3-isoxazolidinone; m.p. 139°-141° C.

Workup

  1. temperaturewhile heating with a steam bath
  2. additionUpon completion of addition the reaction mixture
  3. temperaturewas heated with the steam bath for an additional 30 minutes
  4. filtrationthe resultant solid was collected by filtration
  5. customThe solid was recrystallized from acetone-water

Sources & evidence

ORD record
ord-e9eec82169e74651a9ae4c44ff9f2d6e
Source dataset
uspto-grants-1990_01
Patent number
US04892578

Reaction notes

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