Water → (S)-6-(4-chlorophenyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrazine-2-carboxylic acid

HRID 1025962Notes

Reaction equation

HRID 1025962 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]([O:16]C)=[O:15])[CH:11]=[N:10][C:9]=2[O:18][C@@H:19]([CH3:24])[C:20]([F:23])([F:22])[F:21])=[CH:4][CH:3]=1.[Li+].[OH-].O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]([OH:16])=[O:15])[CH:11]=[N:10][C:9]=2[O:18][C@@H:19]([CH3:24])[C:20]([F:22])([F:21])[F:23])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 66678867(S)-methyl 6-(4-chlorophenyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrazine-2-carboxylate

Product 1

HCID 66678820(S)-6-(4-chlorophenyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrazine-2-carboxylic acidYield 101%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (S)-methyl 6-(4-chlorophenyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrazine-2-carboxylate (0.72 g, 2.00 mmol, Eq: 1.00) in tetrahydrofuran (7 mL) was added a 1M LiOH solution in water (2.59 ml, 2.59 mmol, Eq: 1.3) and the reaction mixture was stirred at room temperature for 1 hour. The mixture was concentrated to remove tetrahydrofuran and diluted with water; acidified with 1M hydrochloric acid to pH 2 and extracted with ethyl acetate. The organic phase was dried with MgSO4; filtered, evaporated and dried to constant weight under high vacuum to yield the title compound as white solid (0.70 g, 100%), MS 345.0 (M−H)−.

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove tetrahydrofuran
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried with MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customdried to constant weight under high vacuum

Sources & evidence

ORD record
ord-d006a3da5eed43e9ae0c8bb3fda6984e
Source dataset
uspto-grants-2014_05
Patent number
US08729105B2

Reaction notes

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