Lithium Hydroxide → 4-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)nicotinic acid

HRID 967965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 967965
C[O:2][C:3](=[O:27])[C:4]1[C:9]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:8][C:7]([CH3:16])=[N:6][C:5]=1[O:17][C:18]1[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=1[CH3:26].[OH-].[Li+]>O1CCOCC1.O>[CH2:12]([CH:11]([NH:10][C:9]1[C:4]([C:3]([OH:27])=[O:2])=[C:5]([O:17][C:18]2[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=2[CH3:26])[N:6]=[C:7]([CH3:16])[CH:8]=1)[CH2:14][CH3:15])[CH3:13]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 232165764-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)nicotinic acid methyl ester

Produkt 1

HCID 218433964-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)nicotinic acidAusbeute 45,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 4-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester (16 mg, 0.043 mmol) and lithium hydroxide (30 mg) in dioxane (1 ml) and water (1 ml) was stirred at rt over night. The mixture was quenched with water and adjusted to pH 7.0 and extracted with chloroform. The organic layer was dried and concentrated to give the crude material. The crude material was purified through silica gel column chromatography using 10% ethyl acetate in chloroform as eluent to give 7 mg of the title compound as white solid. 1H NMR (CDCl3) δ 9.12 (d, 1H), 6.87 (s, 2H), 6.16 (s, 1H), 3.35 (m, 1H), 2.29 (s, 3H), 2.10 (s, 3H), 2.07 (s, 6H), 1.4-1.6 (m, 4H), 0.94 (t, 6H) ppm.

Aufarbeitung

  1. customThe mixture was quenched with water
  2. extractionextracted with chloroform
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customto give the crude material
  6. customThe crude material was purified through silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-dfb48aeb280a4adbb3981b480b0ff001
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06956047B1

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