Hydrochloric Acid → HCID 68816443, compound

HRID 732404Notes

Reaction equation

HRID 732404 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([NH:10][C@H:11]([CH2:13][CH3:14])[CH3:12])[N:7]=[C:6]([C:15](=[O:17])[CH3:16])[CH:5]=1.[OH-].[Li+].Cl>C1COCC1>[C:15]([C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([NH:10][C@H:11]([CH2:13][CH3:14])[CH3:12])[N:7]=1)[C:3]([OH:18])=[O:2])(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68815114HCID 68815114, compound

Product 1

HCID 68816443HCID 68816443, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 2-acetyl-(S)-6-sec-butylamino-isonicotinic acid methyl ester (60 mg, 0.24 mmol) in THF (3 mL). Slowly add 1 N lithium hydroxide (0.3 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 (15 mL) and wash the organic layer with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound as a solid (96%).

Workup

  1. concentrationconcentrate to near dryness
  2. additionDilute with ethyl acetate (15 mL)
  3. washwash the organic layer with saturated aqueous sodium chloride
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-0b5ce413be8a455babe6d1eb747466e0
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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