Ethyl Acetate → Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-methoxypyrazine-2-carboxylate

HRID 467777Notes

Reaction equation

HRID 467777 reaction equation
[C:1]([O:5][C:6]([N:8]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:9]1[C:10]([C:16]([O:18][CH3:19])=[O:17])=[N:11][C:12](Br)=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].[C:30](OCC)(=[O:32])C>CO>[C:1]([O:5][C:6]([N:8]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:9]1[C:10]([C:16]([O:18][CH3:19])=[O:17])=[N:11][C:12]([O:32][CH3:30])=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 86660188Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-bromopyrazine-2-carboxylate

Product 1

HCID 70097371Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-methoxypyrazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(bis(tert-butoxycarbonyl)amino)-6-bromopyrazine-2-carboxylate (500 mg, 1.16 mmol; example A-10, step 1) in MeOH (10 ml) was added sodium methoxide (30%; 280 μl, 1.5 mmol) at room temperature and stirring was continued at r.t. for 2 h. The reaction mixture was poured into ethyl acetate (75 ml) and extracted with potassium hydrogen sulfate (10%). The organic phase was washed with water and brine and the aqueous layers were back-extracted with ethyl acetate. The organic layers were dried and evaporated and the product was obtained after purification by silica gel chromatography using a heptane/ethyl acetate gradient as colorless solid (320 mg, 71%).

Workup

  1. customat room temperature
  2. extractionextracted with potassium hydrogen sulfate (10%)
  3. washThe organic phase was washed with water and brine
  4. extractionthe aqueous layers were back-extracted with ethyl acetate
  5. customThe organic layers were dried
  6. customevaporated
  7. customthe product was obtained
  8. customafter purification by silica gel chromatography

Sources & evidence

ORD record
ord-65b4182698b849dcb411e9623703ffb6
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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