Lithium hydroxide, monohydrate → (5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-yl)-acetic acid

HRID 11678Notes

Reaction equation

HRID 11678 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][C:5]1[C:6]([O:12][CH2:13][C:14]([N:16]2[CH2:21][C@H:20]([CH3:22])[N:19]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH2:18][C@H:17]2[CH3:31])=[O:15])=[N:7][CH:8]=[C:9]([Cl:11])[CH:10]=1.O.[OH-].[Li+]>O1CCCC1.O>[Cl:11][C:9]1[CH:10]=[C:5]([CH2:4][C:3]([OH:32])=[O:2])[C:6]([O:12][CH2:13][C:14]([N:16]2[CH2:21][C@H:20]([CH3:22])[N:19]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH2:18][C@H:17]2[CH3:31])=[O:15])=[N:7][CH:8]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69655283(5-Chloro-2-{2-[4-(4-Fluoro-Benzyl)-(2R,5S)-2,5-Dimethyl-Piperazin-1-Yl]-2-Oxo-Ethoxy}-Pyridin-3-Yl)-Acetic Acid Methyl Ester

Product 1

HCID 69655717(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-yl)-acetic acidYield 45.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-yl)-acetic acid methyl ester (0.14 g, 0.3 mmol) in tetrahydrofuran (3.0 mL) and water (0.6 mL) was added lithium hydroxide monohydrate (0.031 g, 0.75 mmol) at ambient temperature. After stirring for 4 hours the reaction mixture was filtered through a pad of silica gel eluting with 10% methanol/dichloromethane. The filtrate was concentrated in vacuo to provide the title compound (0.061 g).

Workup

  1. filtrationwas filtered through a pad of silica gel eluting with 10% methanol/dichloromethane
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f3976d1097154f9cbbbd5eda043d05d8
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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