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

HRID 1425282Notes

Reaction equation

HRID 1425282 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]3[S:22][C:21]([CH3:23])=[C:20]([C:24]([O:26]C)=[O:25])[CH:19]=3)[CH2:14][C@H:13]2[O:28][CH3:29])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].[OH-].[Li+]>CO.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]3[S:22][C:21]([CH3:23])=[C:20]([C:24]([OH:26])=[O:25])[CH:19]=3)[CH2:14][C@H:13]2[O:28][CH3:29])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67549887HCID 67549887, compound

Product 1

HCID 86648762cis(+/-)-5-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-methylthiophene-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl cis(±)-5-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-methylthiophene-3-carboxylate obtained in Example (188e) (16 mg) was dissolved in methanol (1 ml) and THF (1 ml). A 2 N aqueous lithium hydroxide solution (1 ml) was added, and the mixture was stirred at room temperature overnight. The organic solvent was evaporated under reduced pressure. Then, the residue was neutralized with 1 N hydrochloric acid, diluted with ethyl acetate, washed with brine, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was recrystallized from an ethyl acetate/hexane solvent to obtain the title compound as crystals.

Workup

  1. customThe organic solvent was evaporated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentration under reduced pressure
  6. customthe residue was recrystallized from an ethyl acetate/hexane solvent

Sources & evidence

ORD record
ord-60cbe2ec57b6479087d1628290e62f8d
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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