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

HRID 1776655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1776655
[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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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]+).

Aufarbeitung

  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]+)

Quellen und Nachweise

ORD-Eintrag
ord-d2aa593904fd4f47a81a3d35efc731d8
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09265768B2

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