Hydrochloric Acid → 2-(N-(tert-butoxycarbonyl)methylsulfonamido)isonicotinic acid

HRID 1776655Notes

Reaction equation

HRID 1776655 reaction equation
[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][N:23]=1)[C:16]([O:18]CC)=[O:17])[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][N:23]=1)[C:16]([OH:18])=[O:17])[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 89460062ethyl 2-(N-(tert-butoxycarbonyl)methyl-sulfonamido)isonicotinate

Product 1

HCID 894600592-(N-(tert-butoxycarbonyl)methylsulfonamido)isonicotinic acidYield 74%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-(N-(tert-butoxycarbonyl)methylsulfonamido)isonicotinate (0.920 g, 2.67 mmol) in THF (15 ml), aqueous 1M LiOH (2.94 ml, 2.94 mmol) was added, and the reaction was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate and acidified with aqueous 2N HCl. The organic layer was separated, washed with brine and dried over Na2SO4. The solvent was removed under vacuum and the solid residue was purified by trituration with iPr2O affording after filtration 2-(N-(tert-butoxycarbonyl)methylsulfonamido) isonicotinic acid as a white solid (0.625 g, 1.976 mmol, 74.0% yield, MS/ESI+ 339.2 [MNa]+).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under vacuum
  5. customthe solid residue was purified by trituration with iPr2O affording
  6. filtrationafter filtration 2-(N-(tert-butoxycarbonyl)methylsulfonamido) isonicotinic acid as a white solid (0.625 g, 1.976 mmol, 74.0% yield, MS/ESI+ 339.2 [MNa]+)

Sources & evidence

ORD record
ord-d2aa593904fd4f47a81a3d35efc731d8
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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