Hydrochloric Acid → [4-(3-Cyclopropylpyrazin-2-yl)phenyl]acetic acid

HRID 474145

Reaction equation

HRID 474145 reaction equation
[CH:1]1([C:4]2[C:5]([C:10]3[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19]C)=[O:18])=[CH:12][CH:11]=3)=[N:6][CH:7]=[CH:8][N:9]=2)[CH2:3][CH2:2]1.[Li+].[OH-].Cl>CO>[CH:1]1([C:4]2[C:5]([C:10]3[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=[O:18])=[CH:12][CH:11]=3)=[N:6][CH:7]=[CH:8][N:9]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59535940Methyl [4-(3-cyclopropylpyrazin-2-yl)phenyl]acetate

Product 1

HCID 59535939[4-(3-Cyclopropylpyrazin-2-yl)phenyl]acetic acidYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.10 g (0.37 mmol) of methyl [4-(3-cyclopropylpyrazin-2-yl)phenyl]acetate in 0.75 ml of MeOH was added 0.75 mL (0.75 mmol) of 1N LiOH. After 1 h at room temperature, the reaction mixture was acidified with 1 N HCl, extracted twice with ethyl acetate. The combined organic layers were washed with brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to afforded 0.080 g (84%) of [4-(3-cyclopropylpyrazin-2-yl)phenyl]acetic acid. ES-MS M+1=255.1.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d717518d453149938a13cc4a466f6cf3
Source dataset
uspto-grants-2014_01
Patent number
US08637513B2

Linked notes

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