Lithium Hydroxide → cis(+/-)-2-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-4-(ethylcarbamoyl)-1,3-thiazole-5-carboxylic acid

HRID 1425420Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1425420
[OH-].[Li+].[Cl:3][C:4]1[N:5]=[C:6]([C:11]([NH:13][C@H:14]2[CH2:19][CH2:18][N:17]([C:20]3[S:21][C:22]([C:30]([O:32]CC)=[O:31])=[C:23]([C:25](=[O:29])[NH:26][CH2:27][CH3:28])[N:24]=3)[CH2:16][C@H:15]2[O:35][CH2:36][CH3:37])=[O:12])[NH:7][C:8]=1[CH2:9][CH3:10]>CO>[Cl:3][C:4]1[N:5]=[C:6]([C:11]([NH:13][C@H:14]2[CH2:19][CH2:18][N:17]([C:20]3[S:21][C:22]([C:30]([OH:32])=[O:31])=[C:23]([C:25](=[O:29])[NH:26][CH2:27][CH3:28])[N:24]=3)[CH2:16][C@H:15]2[O:35][CH2:36][CH3:37])=[O:12])[NH:7][C:8]=1[CH2:9][CH3:10]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 86648833Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-4-(ethylcarbamoyl)-1,3-thiazole-5-carboxylate

Produkt 1

HCID 86648834cis(+/-)-2-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-4-(ethylcarbamoyl)-1,3-thiazole-5-carboxylic acidAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A 2 N aqueous lithium hydroxide solution (2.41 mL, 4.82 mmol) was added to a solution of ethyl cis(±)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-4-(ethylcarbamoyl)-1,3-thiazole-5-carboxylate obtained in Example (247a) (254 mg, 0.48 mmol) in methanol (5 mL) at room temperature, followed by stirring for 5.5 hours. The reaction solution was concentrated under reduced pressure, and then a 1 N aqueous hydrochloric acid solution was added to the resulting residue at 0° C. The precipitated solid was collected by filtration, and then washed with water and ethyl acetate to obtain 187 mg of the title compound as a white solid (78%).

Aufarbeitung

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additiona 1 N aqueous hydrochloric acid solution was added to the resulting residue at 0° C
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-630bfbf442f340a2853794fdef75a6c0
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927588B2

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