Hydrochloric Acid → HCID 68814748, compound

HRID 732415Notes

Reaction equation

HRID 732415 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[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]([S:10]([CH3:13])(=[O:12])=[O:11])[N:7]=1)[C:3]([OH:19])=[O:2])([CH2:17][CH3:18])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68815036HCID 68815036, compound

Product 1

HCID 68814748HCID 68814748, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Chill a solution of (S)-2-sec-butylamino-6-methanesulfonyl-isonicotinic acid methyl ester (1.02 g, 3.57 mmol) in THF (10 mL) in an ice bath. Add 1 N lithium hydroxide (5.4 mL, 5.4 mmol) and stir the solution at room temperature for 3 h. Add 1 N HCl until about pH=2. Concentrate and partition the residue between ethyl acetate and water. Separate the layers and extract the aqueous layer with ethyl acetate (2×30 mL). Wash the combined extract with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound.

Workup

  1. concentrationConcentrate
  2. custompartition the residue between ethyl acetate and water
  3. customSeparate the layers
  4. extractionextract the aqueous layer with ethyl acetate (2×30 mL)
  5. washWash the
  6. extractioncombined extract with saturated aqueous sodium chloride
  7. dry with materialdry (magnesium sulfate)
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-7d2a9bb3285a4a0983cbae49f251dc1a
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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