Sodium Hydroxide → (S)-2-sec-Butylamino-6-(2-fluorophenyl)-isonicotinic acid

HRID 732439Notes

Reaction equation

HRID 732439 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[N:7]=[C:6]([NH:17][C@H:18]([CH2:20][CH3:21])[CH3:19])[CH:5]=1.[OH-].[Na+]>CO.C1COCC1>[C@@H:18]([NH:17][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[N:7]=1)[C:3]([OH:22])=[O:2])([CH2:20][CH3:21])[CH3:19]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68815473(S)-2-sec-Butylamino-6-(2-fluorophenyl)-isonicotinic acid methyl ester

Product 1

HCID 68816917(S)-2-sec-Butylamino-6-(2-fluorophenyl)-isonicotinic acidYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Chill a solution of (S)-2-sec-butylamino-6-(2-fluorophenyl)-isonicotinic acid methyl ester (1.31 g, 4.32 mmol) in methanol (5 mL) and THF (5 mL). Add 2 N NaOH (6.50 mL, 13.0 mmol) stir at room temperature for 3 h, and acidify the solution to about pH=2 and concentrate to one half of the solvent. Partition the residue between ethyl acetate and water. Extract the aqueous layer with ethyl acetate (2×30 mL). Wash the combined organic extracts with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound (80%).

Workup

  1. concentrationconcentrate to one half of the solvent
  2. customPartition the residue between ethyl acetate and water
  3. extractionExtract the aqueous layer with ethyl acetate (2×30 mL)
  4. washWash the combined organic extracts with saturated aqueous sodium chloride
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-f2eb39a6d93f4086898e722c14e9b4ff
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

Loading…