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

HRID 1425307

Reaktionsgleichung

Reaktionsgleichung von HRID 1425307
[Cl:1][C@H:2]1[C@@H:7]([NH:8][C:9]([C:11]2[NH:12][C:13]([CH2:17][CH3:18])=[C:14]([Cl:16])[N:15]=2)=[O:10])[CH2:6][CH2:5][N:4]([C:19]2[S:20][C:21]([C:25]([O:27]CC)=[O:26])=[C:22]([CH3:24])[N:23]=2)[CH2:3]1.[OH-].[Li+]>>[Cl:1][C@H:2]1[C@@H:7]([NH:8][C:9]([C:11]2[NH:12][C:13]([CH2:17][CH3:18])=[C:14]([Cl:16])[N:15]=2)=[O:10])[CH2:6][CH2:5][N:4]([C:19]2[S:20][C:21]([C:25]([OH:27])=[O:26])=[C:22]([CH3:24])[N:23]=2)[CH2:3]1

Komponenten

3

Edukt 2

HCID 3939Lithium HydroxideHCID 86648773Ethyl cis(+/-)-2-(3-chloro-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate

Produkt 1

HCID 86648774cis(+/-)-2-(3-Chloro-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylic acidAusbeute 34,2 %

Versuchsvorschrift

The same operation as in Example (2652d) was performed using ethyl cis(±)-2-(3-chloro-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (198c) (78 mg, 0.169 mmol) and a 2 N aqueous lithium hydroxide solution (848 μL). The resulting pale yellow solid was purified by thin layer silica gel chromatography (eluent: chloroform:tetrahydrofuran=3:2 v/v) to obtain 25 mg of the title compound (34%) as a colorless solid from the more polar elution fraction.

Aufarbeitung

  1. customThe resulting pale yellow solid was purified by thin layer silica gel chromatography (eluent: chloroform:tetrahydrofuran=3:2 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-d564025ef0824a14a20dd804d27bae6b
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927588B2

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