Hydrochloric Acid → (S)-2-sec-Butylamino-6-(1,1-difluoroethyl)-isonicotinic acid

HRID 732397Notes

Reaction equation

HRID 732397 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[CH3:11])[N:7]=[C:6]([NH:14][C@H:15]([CH2:17][CH3:18])[CH3:16])[CH:5]=1.[OH-].[Li+].Cl>CO>[C@@H:15]([NH:14][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([C:10]([F:13])([F:12])[CH3:11])[N:7]=1)[C:3]([OH:19])=[O:2])([CH2:17][CH3:18])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68814766(S)-2-sec-Butylamino-6-(1,1-difluoroethyl)-isonicotinic acid methyl ester

Product 1

HCID 68816342(S)-2-sec-Butylamino-6-(1,1-difluoroethyl)-isonicotinic acidYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve (S)-2-sec-butylamino-6-(1,1-difluoroethyl)-isonicotinic acid methyl ester (200 mg, 0.73 mmol) in methanol (3 mL). Slowly add 1 N lithium hydroxide (1.0 mL) and stir overnight at room temperature. Acidify the mixture to about pH=6 by 5 N HCl and concentrate to near dryness. Dilute with ethyl acetate (20 mL) and wash the organic layer with saturated aqueous sodium chloride. Dry (magnesium sulfate) and concentrate to give the title compound as a solid (95%).

Workup

  1. concentrationconcentrate to near dryness
  2. additionDilute with ethyl acetate (20 mL)
  3. washwash the organic layer with saturated aqueous sodium chloride
  4. dry with materialDry (magnesium sulfate)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-b1d2f76bb07140a2a23dfc74383295d8
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

Loading…