Hydrochloric Acid → HCID 68814740, compound

HRID 732402Notes

Reaction equation

HRID 732402 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-bdd9c0613f8f4014b5d756b773a157aa
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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