Potassium Hydroxide → 5-[(Tert-butoxy)carbonyl]pyrazine-2-carboxylic acid

HRID 1878374Notes

Reaction equation

HRID 1878374 reaction equation
[C:1]([O:5][C:6]([C:8]1[N:9]=[CH:10][C:11]([C:14]([O:16]CC)=[O:15])=[N:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>CO>[C:1]([O:5][C:6]([C:8]1[N:9]=[CH:10][C:11]([C:14]([OH:16])=[O:15])=[N:12][CH:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 66878222HCID 66878222, compound

Product 1

HCID 668782615-[(Tert-butoxy)carbonyl]pyrazine-2-carboxylic acidYield 97.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of ethyl 5(tert-butoxycarbonyl)pyrazine-2-carboxylate (0.742 g, 2.78 mmol) and methanol (20 mL) was added potassium hydroxide (0.23 g, 4.1 mmol) in wafer (2 mL) and the reaction was stirred at room temperature overnight. The solvent was removed under vacuum and the residue was dissolved in wafer (5 mL) and acidified to pH 2 with 1M hydrochloric acid. The solid precipitate was collected by filtration to afford the title compound (0.61 g). MS (ESI) m/z 240.2 [M+H]+

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in wafer (5 mL)
  3. filtrationThe solid precipitate was collected by filtration

Sources & evidence

ORD record
ord-d026c8b85c554e698687b34701d92487
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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