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

HRID 1436531Notes

Reaction equation

HRID 1436531 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([N:10]([S:12]([CH:15]2[CH2:17][CH2:16]2)(=[O:14])=[O:13])[CH3:11])[N:7]=[C:6]([NH:18][C@H:19]([CH2:21][CH3:22])[CH3:20])[CH:5]=1.[OH-].[Na+].Cl>CO>[C@@H:19]([NH:18][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([N:10]([S:12]([CH:15]2[CH2:16][CH2:17]2)(=[O:13])=[O:14])[CH3:11])[N:7]=1)[C:3]([OH:23])=[O:2])([CH2:21][CH3:22])[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68815532(S)-2-sec-Butylamino-6-(cyclopropanesulfonyl-methylamino)-isonicotinic acid methyl ester

Product 1

HCID 68816222(S)-2-sec-Butylamino-6-(cyclopropanesulfonyl-methylamino)-isonicotinic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve (S)-2-sec-butylamino-6-(cyclopropanesulfonyl-methylamino)-isonicotinic acid methyl ester (600 mg, 1.97 mmol) in methanol (18 mL). Slowly add 2 N NaOH (3 mL) and stir overnight at room temperature. Acidify the mixture to about pH=6 with 5 N HCl and concentrate. Dilute with ethyl acetate (30 mL) and wash the organic layer with saturated aqueous sodium chloride solution, dry (magnesium sulfate) and concentrate to give the title compound.

Workup

  1. concentrationconcentrate
  2. additionDilute with ethyl acetate (30 mL)
  3. washwash the organic layer with saturated aqueous sodium chloride solution
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-4ec07f6656644a06b6ca764ee73f6398
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

Loading…