Sodium Acetate → HCID 19794299, compound

HRID 465746Notes

Reaction equation

HRID 465746 reaction equation
[C:1]([O:4][CH2:5][CH:6]1[CH:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[CH2:8][CH:7]1[N:15]1[CH:23]=[N:22][C:21]2[C:16]1=[N:17][C:18]([NH2:25])=[N:19][C:20]=2Cl)(=[O:3])[CH3:2].C([O-])(=O)C.[Na+].[H][H]>[Pd].CO>[C:1]([O:4][CH2:5][CH:6]1[CH:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[CH2:8][CH:7]1[N:15]1[CH:23]=[N:22][C:21]2[C:16]1=[N:17][C:18]([NH2:25])=[N:19][CH:20]=2)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 19875576HCID 19875576, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19794299HCID 19794299, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2.63 g (7.15 mmol) of the product from Example 22, 1.18 g (14.3 mmol) of anhydrous sodium acetate, 1.0 g of 10% Pd on carbon and 100 mL of methanol was stirred under 1 atmosphere of hydrogen. After 12 hours, the reaction mixture was filtered and concentrated to a residue under reduced pressure. To the residue was added water and ethyl acetate, and the phases were separated. The aqueous phase was extracted with several portions of ethyl acetate and the combined organic extracts were concentrated under reduced pressure. Chromatography of the residue on silica gel with a 100:0 to 90:10/ethyl acetate:methanol gradient afforded 1.60 g (67%) of the title compound as an oil. DCI-NH3MS, m/z 334 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated to a residue under reduced pressure
  3. additionTo the residue was added water and ethyl acetate
  4. customthe phases were separated
  5. extractionThe aqueous phase was extracted with several portions of ethyl acetate
  6. concentrationthe combined organic extracts were concentrated under reduced pressure

Sources & evidence

ORD record
ord-666c9a770c364df9805139a0783aec8d
Source dataset
uspto-grants-1992_10
Patent number
US05153352

Reaction notes

Loading…