Sodium Hydroxide → HCID 68817200, compound

HRID 732421Notes

Reaction equation

HRID 732421 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:23])[C:6]1[CH:11]=[C:10]([S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[N:9]=[C:8]([NH:18][CH:19]([CH2:21][CH3:22])[CH3:20])[CH:7]=1>CO>[C@@H:19]([NH:18][C:8]1[CH:7]=[C:6]([CH:11]=[C:10]([S:12]([CH:15]([CH3:16])[CH3:17])(=[O:14])=[O:13])[N:9]=1)[C:5]([OH:23])=[O:4])([CH2:21][CH3:22])[CH3:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68815842HCID 68815842, compound

Product 1

HCID 68817200HCID 68817200, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 2 N NaOH (7.0 mL, 14.0 mmol) to a solution of 2-sec-butylamino-6-isopropanesulfonyl-isonicotinic acid methyl ester (1.46 g, 4.65 mmol) in methanol (10 mL) at 0° C. Stir the mixture at room temperature for 3 h and acidify the solution to about pH=2 and concentrate the solvent to one half volume. Partition the residue between ethyl acetate and water, and extract the aqueous layer with ethyl acetate (2×50 mL). Wash the combined organic extracts with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound in 90% yield.

Workup

  1. concentrationconcentrate the solvent to one half volume
  2. customPartition the residue between ethyl acetate and water
  3. extractionextract the aqueous layer with ethyl acetate (2×50 mL)
  4. washWash the combined organic extracts with saturated aqueous sodium chloride
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-629cf0e9c41841d78605c146a201756b
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

Loading…