Hydrochloric Acid → HCID 68814748, compound

HRID 1436559Notes

Reaction equation

HRID 1436559 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-202542c0494f4541bfac154d697ae3a4
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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