Hydrochloric Acid → AM-432

HRID 1625676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1625676
C([O:3][C:4](=[O:38])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[N:22][C:23]([O:26][CH2:27][CH3:28])=[CH:24][CH:25]=3)=[CH:16][C:15]=2[CH2:29][N:30]([C:33]([CH:35]2[CH2:37][CH2:36]2)=[O:34])[CH2:31][CH3:32])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)C.[OH-].[Li+].Cl>O1CCCC1.O>[CH:35]1([C:33]([N:30]([CH2:29][C:15]2[CH:16]=[C:17]([C:20]3[CH:21]=[N:22][C:23]([O:26][CH2:27][CH3:28])=[CH:24][CH:25]=3)[CH:18]=[CH:19][C:14]=2[C:8]2[C:9]([O:12][CH3:13])=[CH:10][CH:11]=[C:6]([CH2:5][C:4]([OH:38])=[O:3])[CH:7]=2)[CH2:31][CH3:32])=[O:34])[CH2:36][CH2:37]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58149167[2'-[(Cyclopropanecarbonyl-ethyl-amino)-methyl]-4'-(6-ethoxy-pyridin-3-yl)-6-methoxy-biphenyl-3-yl]-acetic acid ethyl ester

Produkt 1

HCID 50901658AM-432

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

[2′-[(cyclopropanecarbonyl-ethyl-amino)-methyl]-4′-(6-ethoxy-pyridin-3-yl)-6-methoxy-biphenyl-3-yl]-acetic acid ethyl ester (32.7 g, 63.3 mmol) in tetrahydrofuran (150 mL) and water (75 mL) was treated with lithium hydroxide (8.0 g, 190.6 mmol) and the reaction was stirred at room temperature overnight. When the reaction was complete by analytical LCMS, the mixture was acidified with 1N aqueous hydrochloric acid to pH 3 and extracted 2 times with dichloromethane. The combined organic layers were dried over magnesium sulfate and concentrated to afford the title compound as an off-white foam.

Aufarbeitung

  1. extractionextracted 2 times with dichloromethane
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ea2a4e78adc344fd810e08c935200fe2
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785393B2

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