Lithium Hydroxide → HCID 68818120, compound

HRID 732437Notes

Reaction equation

HRID 732437 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:22])[C:6]1[CH:11]=[C:10]([S@:12]([CH2:14][CH2:15][CH3:16])=[O:13])[N:9]=[C:8]([NH:17][CH:18]([CH2:20][CH3:21])[CH3:19])[CH:7]=1>C1COCC1>[CH:18]([NH:17][C:8]1[CH:7]=[C:6]([CH:11]=[C:10]([S@:12]([CH2:14][CH2:15][CH3:16])=[O:13])[N:9]=1)[C:5]([OH:22])=[O:4])([CH2:20][CH3:21])[CH3:19]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68815368HCID 68815368, compound

Product 1

HCID 68818120HCID 68818120, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 1 N lithium hydroxide (1.15 mL, 1.15 mmol) to a solution of (S)-2-sec-butylamino-6-(propane-1-sulfinyl)-isonicotinic acid methyl ester (0.229 g, 0.767 mmol) in THF (2 mL) at 0° C. Stir at room temperature for 3 h, acidify the solution to about pH=2 and concentrate to one half of the solvent. Partition the residue between ethyl acetate and water. Extract the aqueous layer with ethyl acetate (2×10 mL). Wash the combine organic extract with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound (95%).

Workup

  1. concentrationconcentrate to one half of the solvent
  2. customPartition the residue between ethyl acetate and water
  3. extractionExtract the aqueous layer with ethyl acetate (2×10 mL)
  4. washWash the combine
  5. extractionorganic extract with saturated aqueous sodium chloride
  6. dry with materialdry (magnesium sulfate)
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-54e1414478c9457b99c08200849819b3
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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