Lithium Hydroxide → (S)-2-sec-Butylamino-6-(methanesulfonyl-methylamino)-isonicotinic acid

HRID 1436572Notes

Reaction equation

HRID 1436572 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:23])[C:6]1[CH:11]=[C:10]([N:12]([S:14]([CH3:17])(=[O:16])=[O:15])[CH3:13])[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]([N:12]([S:14]([CH3:17])(=[O:16])=[O:15])[CH3:13])[N:9]=1)[C:5]([OH:23])=[O:4])([CH2:21][CH3:22])[CH3:20]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68814724(S)-2-sec-Butylamino-6-(methanesulfonyl-methylamino)-isonicotinic acid methyl ester

Product 1

HCID 68815290(S)-2-sec-Butylamino-6-(methanesulfonyl-methylamino)-isonicotinic acidYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 1 N lithium hydroxide (19.5 mL, 19.5 mmol) to a solution of (S)-2-sec-butylamino-6-(methanesulfonyl-methylamino)-isonicotinic acid methyl ester (2.45 g, 7.77 mmol) in THF (10 mL) at 0° C. After 2 h at room temperature, acidify the mixture to about pH =2 and concentrate. Extract the residue with ethyl acetate (3×40 mL), wash the combined extracts with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound as a yellow solid (2.23 g, 95%).

Workup

  1. concentrationconcentrate
  2. extractionExtract the residue with ethyl acetate (3×40 mL)
  3. washwash the combined extracts with saturated aqueous sodium chloride
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-98221ea8ece5427fb4fbd7fc7163685a
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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