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 43950Notes

Reaction equation

HRID 43950 reaction equation
[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]

Participants

4

Reactant 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

Product 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 acidYield 78.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-09d0140661c844bf8aee6cccace19f71
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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