Lithium hydroxide, monohydrate → 6-(((Tert-butoxy)carbonyl)(ethyl)amino)pyridine-3-carboxylic acid

HRID 1874068

Reaktionsgleichung

Reaktionsgleichung von HRID 1874068
C[O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH3:12])=[N:6][CH:5]=1.O.[OH-].[Li+]>O1CCOCC1.O>[C:16]([O:15][C:13]([N:10]([CH2:11][CH3:12])[C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:20])=[O:2])=[CH:5][N:6]=1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 667701426-(Tert-butoxycarbonyl-ethyl-amino)-nicotinic acid methyl ester

Produkt 1

HCID 667695526-(((Tert-butoxy)carbonyl)(ethyl)amino)pyridine-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

The crude 6-(tert-butoxycarbonyl-ethyl-amino)-nicotinic acid methyl ester is taken up in 100 mL dioxane and a solution of lithium hydroxide monohydrate (13.5 g, 0.32 mol) in 100 mL water is added and the reaction mixture is stirred at RT for 4 h. The dioxane is removed from the reaction mixture under reduced pressure, water is added and the reaction mixture is acidified to pH 6 with a solution of 10% citric acid in water. The formed precipitate is filtered off and dried in vacuo. Yield: 36 g. 1H NMR (DMSO-d6): δ 13.2 (s, 1H), 8.8 (s, 1H), 8.2 (d, 1H), 7.8 (d, 1H), 4.0 (quart, 2H), 1.5 (s, 9H), 1.2 (t, 3H).

Aufarbeitung

  1. customThe dioxane is removed from the reaction mixture under reduced pressure, water
  2. additionis added
  3. filtrationThe formed precipitate is filtered off
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d0e12d01cb314f60a742f161c019c64b
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304556B2

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