Hydrochloric Acid → 2-sec-Butylamino-6-methanesulfonyloxy-isonicotinic acid

HRID 1436614Notes

Reaction equation

HRID 1436614 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:22])[C:6]1[CH:11]=[C:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[N:9]=[C:8]([NH:17][CH:18]([CH2:20][CH3:21])[CH3:19])[CH:7]=1.Cl>C1COCC1>[CH:18]([NH:17][C:8]1[CH:7]=[C:6]([CH:11]=[C:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[N:9]=1)[C:5]([OH:22])=[O:4])([CH2:20][CH3:21])[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 866150112-sec-Butylamino-6-methanesulfonyloxy-isonicotinic acid methyl ester

Product 1

HCID 866150122-sec-Butylamino-6-methanesulfonyloxy-isonicotinic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 1 N lithium hydroxide (2 mL) to a solution of 2-sec-butylamino-6-methanesulfonyloxy-isonicotinic acid methyl ester (235 mg, 0.743 mmol) in THF (15 mL) at 0° C. Warm to room temperature and stir for 12 h. Acidify with 5% aqueous HCl to about pH=3, extract with ethyl acetate, dry (magnesium sulfate), and concentrate to give the title compound.

Workup

  1. extractionextract with ethyl acetate
  2. dry with materialdry (magnesium sulfate)
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-02d37223f98c464c9fce56ded617f9ee
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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