Hydrochloric Acid → cis(+/-)-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)(oxo)acetic acid

HRID 43722Notes

Reaction equation

HRID 43722 reaction equation
[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](=[O:24])[C:19]([O:21]CC)=[O:20])[CH2:14][C@H:13]2[O:25][CH2:26][CH3:27])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].[OH-].[Na+].Cl>C1COCC1>[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](=[O:24])[C:19]([OH:21])=[O:20])[CH2:14][C@H:13]2[O:25][CH2:26][CH3:27])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86648672Ethyl cis(+/-)-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)(oxo)acetate

Product 1

HCID 86648671cis(+/-)-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)(oxo)acetic acidYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl cis(±)-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)(oxo)acetate obtained in Example (132a) (122 mg, 0.316 mmol) was dissolved in THF (3 mL). A 1 N aqueous sodium hydroxide solution (0.95 ml, 0.95 mmol) was added, and the mixture was stirred at room temperature for 1.5 hours. The reaction solution was neutralized with 1 N hydrochloric acid and concentrated under reduced pressure. Then, the residue was purified by preparative HPLC (TSK-gel, Toso, elution solvent: water/acetonitrile=17/3→1/1) to obtain 79.8 mg of the title compound as a colorless amorphous solid (68%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThen, the residue was purified by preparative HPLC (TSK-gel, Toso, elution solvent: water/acetonitrile=17/3→1/1)

Sources & evidence

ORD record
ord-f3dbe2bc760940f8b9113530239a9dbb
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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