Hydrochloric Acid → (S)-2-sec-Butylamino-6-difluoromethyl-isonicotinic acid

HRID 732394Notes

Reaction equation

HRID 732394 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([CH:10]([F:12])[F:11])[N:7]=[C:6]([NH:13][CH:14]([CH2:16][CH3:17])[CH3:15])[CH:5]=1.[OH-].[Li+].Cl>CO.C1COCC1>[C@@H:14]([NH:13][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([CH:10]([F:12])[F:11])[N:7]=1)[C:3]([OH:18])=[O:2])([CH2:16][CH3:17])[CH3:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 688142752-Sec-butylamino-6-difluoromethyl-isonicotinic acid methyl ester

Product 1

HCID 68815849(S)-2-sec-Butylamino-6-difluoromethyl-isonicotinic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 2-sec-butylamino-6-difluoromethyl-isonicotinic acid methyl ester (140 mg, 0.54 mmol) in methanol (2 mL) and THF (10 mL). Slowly add 1 N aqueous lithium hydroxide (0.7 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.

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-4e5ceb5597e64f8d95fdbd4702b76fc6
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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