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

HRID 732400Notes

Reaction equation

HRID 732400 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([CH2:10][C:11](=[O:13])[CH3:12])[N:7]=[C:6]([NH:14][C@H:15]([CH2:17][CH3:18])[CH3:16])[CH:5]=1.[OH-].[Li+].Cl>C1COCC1>[C@@H:15]([NH:14][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([CH2:10][C:11](=[O:13])[CH3:12])[N:7]=1)[C:3]([OH:19])=[O:2])([CH2:17][CH3:18])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68814857(S)-2-sec-Butylamino-6-(2-oxopropyl)-isonicotinic acid methyl ester

Product 1

HCID 68818395(S)-2-sec-Butylamino-6-(2-oxopropyl)-isonicotinic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve (S)-2-sec-butylamino-6-(2-oxopropyl)-isonicotinic acid methyl ester (50 mg, 0.19 mmol) in THF (2 mL). Slowly add 1 N lithium hydroxide (0.28 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 (10 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 (10 mL)
  3. washwash the organic layer with saturated aqueous sodium chloride
  4. dry with materialDry (magnesium sulfate)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-ae831b0ee47b4419a1e96bbbdfbd0f29
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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