Lithium Hydroxide → HCID 68814991, compound

HRID 732431Notes

Reaction equation

HRID 732431 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:23])[C:6]1[CH:11]=[C:10]([S:12](=[O:17])(=[O:16])[N:13]([CH3:15])[CH3:14])[N:9]=[C:8]([NH:18][C@H:19]([CH2:21][CH3:22])[CH3:20])[CH:7]=1>C1COCC1>[C@@H:19]([NH:18][C:8]1[CH:7]=[C:6]([CH:11]=[C:10]([S:12](=[O:17])(=[O:16])[N:13]([CH3:14])[CH3:15])[N:9]=1)[C:5]([OH:23])=[O:4])([CH2:21][CH3:22])[CH3:20]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68814982HCID 68814982, compound

Product 1

HCID 68814991HCID 68814991, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 1 N lithium hydroxide (11.4 mL, 11.4 mmol) to a solution of (S)-2-sec-butylamino-6-dimethylsulfamoyl-isonicotinic acid methyl ester (1.43 g, 4.54 mmol) and THF (10 mL) at 0° C. Stir the mixture overnight, acidify the solution to about pH=2 and concentrate solvent to one half volume. Partition the residue between ethyl acetate and water, and extract the aqueous layer with ethyl acetate (2×30 mL). Wash the combined organic extract with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound.

Workup

  1. concentrationconcentrate solvent to one half volume
  2. customPartition the residue between ethyl acetate and water
  3. extractionextract the aqueous layer with ethyl acetate (2×30 mL)
  4. washWash the combined
  5. extractionorganic extract with saturated aqueous sodium chloride
  6. dry with materialdry (magnesium sulfate)
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-0a0373ebc50049308b6f9ce3f591a93e
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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