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

HRID 1967048
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1967048
C([O:3][C:4](=[O:41])[CH2:5][CH2:6][NH:7][C:8](=[O:40])[C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([O:16][C:17]2[C:22]([C:23]([N:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]([CH:35]4[CH2:37][CH2:36]4)[CH2:27][CH2:26]3)=[O:24])=[CH:21][N:20]=[C:19]([CH3:38])[CH:18]=2)=[CH:11][C:10]=1[Cl:39])C.O.O.[OH-].[Li+].Cl>O1CCOCC1.C(OCC)(=O)C>[Cl:39][C:10]1[CH:11]=[C:12]([O:16][C:17]2[C:22]([C:23]([N:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]([CH:35]4[CH2:37][CH2:36]4)[CH2:27][CH2:26]3)=[O:24])=[CH:21][N:20]=[C:19]([CH3:38])[CH:18]=2)[C:13]([Cl:15])=[CH:14][C:9]=1[C:8]([NH:7][CH2:6][CH2:5][C:4]([OH:41])=[O:3])=[O:40]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 533114503-{2,5-Dichloro-4-[5-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-2-methyl-pyridin-4-yloxy]-benzoylamino}-propionic acid ethyl ester

Produkt 1

HCID 533115343-{2,5-Dichloro-4-[5-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-2-methyl-pyridin-4-yloxy]-benzoylamino}-propionic acid
Ausbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 83 mg (0.139 mmol) 3-{2,5-dichloro-4-[5-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-2-methyl-pyridin-4-yloxy]-benzoylamino}-propionic acid ethyl ester in 2 mL dioxane was added 2 mL water and 7 mg (0.174 mmol) lithium hydroxide monohydrate. The reaction mixture was stirred for 4 hours at room temperature. The reaction mixture was poured on 20 mL 1N aqueous hydrochloric acid and 20 mL ethyl acetate and the layers were separated. The aqueous layer was extracted with 20 mL ethyl acetate and the organic layers were washed with 30 mL brine, dried over magnesium sulfate, filtered and concentrated under vacuum to give the title compound as a light yellow solid (100%). MS (ESI): m/z=569.136 [M+H]+.

Aufarbeitung

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with 20 mL ethyl acetate
  3. washthe organic layers were washed with 30 mL brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4cc4a9b5579f4393aed42ff3a986673d
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08420647B2

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