Water → 3-{2,5-Dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoylamino}-propionic acid

HRID 1967014

Reaktionsgleichung

Reaktionsgleichung von HRID 1967014
C([O:3][C:4](=[O:40])[CH2:5][CH2:6][NH:7][C:8](=[O:39])[C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([O:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][C:18]=2[C:23]([N:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]([CH:35]3[CH2:37][CH2:36]3)[CH2:27][CH2:26]2)=[O:24])=[CH:11][C:10]=1[Cl:38])C.O.O.[OH-].[Li+]>O1CCOCC1>[Cl:38][C:10]1[CH:11]=[C:12]([O:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][C:18]=2[C:23]([N:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]([CH:35]3[CH2:37][CH2:36]3)[CH2:27][CH2:26]2)=[O:24])[C:13]([Cl:15])=[CH:14][C:9]=1[C:8]([NH:7][CH2:6][CH2:5][C:4]([OH:40])=[O:3])=[O:39]

Komponenten

5

Edukt 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 533122803-{2,5-Dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoylamino}-propionic acid ethyl ester

Produkt 1

HCID 533122813-{2,5-Dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoylamino}-propionic acidAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 0.85 g (1.46 mmol) 3-{2,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoylamino}-propionic acid ethyl ester (Example 33) in 7.5 mL dioxane were added 7.5 mL water and 0.076 g (1.81 mmol) lithium hydroxide monohydrate. The resulting suspension was stirred for 2.25 hours at room temperature and dioxane was removed by evaporation. The pH of the solution was adjusted to 2.5 by adding 1.9 mL 1M aqueous hydrochloric acid and the suspension was stirred for 2 hours at room temperature. The suspension was filtered, the filter cake washed with water and dried under high vacuum to give 0.70 g (86%) of the desired compound as an off-white solid. MS (ESI): m/z=555.12 [M+H]+.

Aufarbeitung

  1. customdioxane was removed by evaporation
  2. additionby adding 1.9 mL 1M aqueous hydrochloric acid
  3. stirringthe suspension was stirred for 2 hours at room temperature
  4. filtrationThe suspension was filtered
  5. washthe filter cake washed with water
  6. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5e02d2565cc0495cbb52ed7e2a34636e
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420647B2

Verknüpfte Notizen

Wird geladen…