Lithium Hydroxide → cis(+/-)-2-{3-(Benzyloxy)-4-[(1H-imidazol-2-ylcarbonyl)amino]piperidin-1-yl}-1,3-thiazole-5-carboxylic acid

HRID 43558

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

Ethyl cis(±)-2-{3-(benzyloxy)-4-[(1H-imidazol-2-ylcarbonyl)amino]piperidin-1-yl}-1,3-thiazole-5-carboxylate obtained in Example (90f) (0.25 g, 0.55 mmol) was dissolved in methanol (5 mL) and dichloromethane (1 mL). A 2 N aqueous lithium hydroxide solution (5 mL, 10 mmol) was added, and the mixture was stirred at 70° C. for 20 minutes. The organic solvent was evaporated under reduced pressure, and 1 N hydrochloric acid was added until the pH of the solution was about 4. Purification by reverse phase chromatography (elution solvent: acetonitrile/water=1/1, 4/1) gave 0.15 g of the title compound as a white solid (66%).

Workup

customThe organic solvent was evaporated under reduced pressure, and 1 N hydrochloric acid
additionwas added until the pH of the solution
customPurification
washby reverse phase chromatography (elution solvent: acetonitrile/water=1/1, 4/1)

Sources & evidence

ORD record: ord-28c11b907bf24a818479a4c20316c540
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536197B2

Linked notes

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