Hydrochloric Acid → HCID 68814740, compound

HRID 1436546Notes

Reaction equation

HRID 1436546 reaction equation
C[O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([CH2:10][C:11]([F:14])([F:13])[CH3:12])[N:7]=[C:6]([NH:15][C@H:16]([CH2:18][CH3:19])[CH3:17])[CH:5]=1.[OH-].[Li+].Cl>C1COCC1>[C@@H:16]([NH:15][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([CH2:10][C:11]([F:14])([F:13])[CH3:12])[N:7]=1)[C:3]([OH:20])=[O:2])([CH2:18][CH3:19])[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68815041HCID 68815041, compound

Product 1

HCID 68814740HCID 68814740, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve (S)-2-sec-butylamino-6-(2,2-difluoropropyl)-isonicotinic acid methyl ester (100 mg, 0.34 mmol) in THF (3 mL). Slowly add 1 N lithium hydroxide (0.52 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-3466a4f5013746c6b2ffdee7aac56836
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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