Tert-butyl 2-(3-chloropyrazin-2-yl)-2-methylpropanoate → 2-(3-Chloropyrazin-2-yl)-2-methylpropanoic acid

HRID 707237Notes

Reaction equation

HRID 707237 reaction equation
[Cl:1][C:2]1[C:3]([C:8]([CH3:17])([CH3:16])[C:9]([O:11]C(C)(C)C)=[O:10])=[N:4][CH:5]=[CH:6][N:7]=1>ClCCl.FC(F)(F)C(O)=O>[Cl:1][C:2]1[C:3]([C:8]([CH3:17])([CH3:16])[C:9]([OH:11])=[O:10])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

4

Reactant 1

HCID 86694117Tert-butyl 2-(3-chloropyrazin-2-yl)-2-methylpropanoate

Product 1

HCID 866941182-(3-Chloropyrazin-2-yl)-2-methylpropanoic acidYield 59.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The tert-butyl ester from step 1 was dissolved in a mixture of dichloromethane (40 mL) and trifluoroacetic acid (20 mL) and heated at reflux. After 4 hours the solution was evaporated to dryness under reduced pressure and purified using silica chromatography (0-10% methanol in dichloromethane gradient) to give 2-(3-chloropyrazin-2-yl)-2-methylpropanoic acid (5.70 g, 28.4 mmol, 59.2% yield) as a tan solid.

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. customAfter 4 hours the solution was evaporated to dryness under reduced pressure
  4. custompurified

Sources & evidence

ORD record
ord-ce57420ac431467b8351bc0c4c277f08
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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