Sodium Hydroxide → HCID 68815078, compound

HRID 1436563Notes

Reaction equation

HRID 1436563 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:23])[C:6]1[CH:11]=[C:10]([S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])[N:9]=[C:8]([NH:18][C@H: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]([CH2:15][CH2:16][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 68816237HCID 68816237, compound

Product 1

HCID 68815078HCID 68815078, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 2 N NaOH (6.0 mL, 12.0 mmol) to a solution of (S)-2-sec-butylamino-6-propanesulfonyl-isonicotinic acid methyl ester (2.47 g, 7.87 mmol) in methanol (10 mL) at 0° C. Stir the mixture 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 (2×50 mL). Wash the combined extracts with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound (90%).

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 (2×50 mL)
  4. washWash the combined extracts with saturated aqueous sodium chloride
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-9c7ba63dd3de42d482f80bb8c40cb262
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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