Sodium Hydroxide → HCID 54357753, compound

HRID 2255160Notes

Reaction equation

HRID 2255160 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[C:12]([CH2:24][CH:25]([CH3:27])[CH3:26])=[N+:13]([O-:23])[C:14]([O:21][CH3:22])=[C:15]([C:17]([O:19]C)=[O:18])[N:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO.O>[CH2:3]([O:10][C:11]1[N:16]=[C:15]([C:17]([OH:19])=[O:18])[C:14]([O:21][CH3:22])=[N+:13]([O-:23])[C:12]=1[CH2:24][CH:25]([CH3:27])[CH3:26])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10970054HCID 10970054, compound

Product 1

HCID 54357753HCID 54357753, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4.1 Milliliters of 1N sodium hydroxide was added to a solution of 0.71 g of 3-benzyloxy-2-isobutyl-6-methoxy-5-methoxycarbonylpyrazine 1-oxide dissolved in 15 ml of methanol, then the mixture was stirred for 14 hours at room temperature. The reaction mixture was diluted with water, and then extracted with dichloromethane. The aqueous layer was made acidic with 6.0 ml of 1N hydrochloric acid with ice cooling, then extracted with ethyl acetate. The extract was washed with an aqueous solution saturated with NaCl twice and dried over magnesium sulfate. The solvent was removed by evaporation to obtain 0.62 g of 6-benzyloxy-5-isobutyl-3-methoxypyrazine-2-carboxylic acid 4-oxide (Compound B-22).

Workup

  1. extractionextracted with dichloromethane
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with an aqueous solution saturated with NaCl twice
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-0c8be6ca5812449284d29984194807ad
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

Loading…