Sodium Acetate → HCID 9927359, compound

HRID 1167617Notes

Reaction equation

HRID 1167617 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][CH:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:8]([CH2:18][C:19]#[N:20])[C:7]=2[CH:21]=1.[C:22]([O-])(=[O:24])[CH3:23].[Na+]>C(OC(=O)C)(=O)C.[Ni]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][CH:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:8]([CH2:18][CH2:19][NH:20][C:22](=[O:24])[CH3:23])[C:7]=2[CH:21]=1

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 22993355HCID 22993355, compound

Product 1

HCID 9927359HCID 9927359, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

The compound obtained in Step C (200 mg; 0.71 mmol) is dissolved in a Parr reactor with acetic anhydride. Raney nickel (30% by weight, 60 mg) and sodium acetate (1.5 eq.; 1.07 mmol; 88 mg) are then added. The mixture is left at 50° C. for 36 hours under a hydrogen pressure of 40 psi. After returning to ambient temperature, the solution is filtered over Celite and the filtrate is evaporated. The crude reaction product is purified by flash chromatography on silica gel (eluant: AcOEt). The title product is obtained in the form of white crystals, which are recrystallised from an Et2O/i-PrOH mixture.

Workup

  1. customAfter returning to ambient temperature
  2. filtrationthe solution is filtered over Celite
  3. customthe filtrate is evaporated
  4. customThe crude reaction product
  5. customis purified by flash chromatography on silica gel (eluant: AcOEt)

Sources & evidence

ORD record
ord-c16e6e4eeb114ff39a660d848ddabed1
Source dataset
uspto-grants-2003_09
Patent number
US06620809B2

Reaction notes

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