Lithium Hydroxide → cis(+/-)-2-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-benzothiazole-7-carboxylic acid

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Reaktionsgleichung

[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][N:15]([C:18]3[S:19][C:20]4[C:26]([C:27]([O:29]CC)=[O:28])=[CH:25][CH:24]=[CH:23][C:21]=4[N:22]=3)[CH2:14][C@H:13]2[O:32][CH3:33])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].[OH-].[Li+]>CO.ClCCl>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][N:15]([C:18]3[S:19][C:20]4[C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=[CH:23][C:21]=4[N:22]=3)[CH2:14][C@H:13]2[O:32][CH3:33])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

Ethyl cis(±)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-benzothiazole-7-carboxylate obtained in Example (1h) (95 mg, 0.19 mmol) was dissolved in methanol (5 mL) and dichloromethane (2 mL). A 2 N aqueous lithium hydroxide solution (3 mL) was added, and the mixture was stirred at 70° C. for 1.5 hours. The organic solvent was evaporated under reduced pressure and 1 N hydrochloric acid was added until the pH of the solution was about 4. The resulting solid was collected by filtration and washed with distilled water to obtain 75 mg of the title compound as a white solid (84%).

Aufarbeitung

customThe organic solvent was evaporated under reduced pressure and 1 N hydrochloric acid
additionwas added until the pH of the solution
filtrationThe resulting solid was collected by filtration
washwashed with distilled water

Quellen und Nachweise

ORD-Eintrag: ord-c5672af4f63b4da0b1bc9dccff89d313
Quelldatensatz: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08927588B2

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