Lithium Hydroxide → (S)-5-(4-Chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)nicotinic acid

HRID 1025964Notes

Reaction equation

HRID 1025964 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:18][C@@H:19]([CH3:24])[C:20]([F:23])([F:22])[F:21])=[N:10][CH:11]=[C:12]([CH:17]=2)[C:13]([O:15]C)=[O:14])=[CH:4][CH:3]=1.[OH-].[Li+]>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([O:18][C@@H:19]([CH3:24])[C:20]([F:23])([F:21])[F:22])=[N:10][CH:11]=[C:12]([CH:17]=2)[C:13]([OH:15])=[O:14])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66678826(S)-methyl 5-(4-chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)nicotinate

Product 1

HCID 66678484(S)-5-(4-Chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)nicotinic acidYield 100.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.860 g (S)-methyl 5-(4-chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)nicotinate in 9 mL tetrahydrofuran was added 3 mL of a 1M solution of lithium hydroxide in water and the mixture was stirred at room temperature overnight. The solvent was evaporated and the residue was acidified by addition of 1M hydrochloric acid till pH=2. Ethyl acetate was added and the phases were separated. The organic phase was dried over MgSO4 and the solvent was removed to yield 830 mg (100%) of the title compound as light yellow solid, MS 344.1 (M−H)−.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was acidified by addition of 1M hydrochloric acid till pH=2
  3. additionEthyl acetate was added
  4. customthe phases were separated
  5. dry with materialThe organic phase was dried over MgSO4
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-44a5f098249948d787ee0ab09fb7da40
Source dataset
uspto-grants-2014_05
Patent number
US08729105B2

Reaction notes

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