Lithium hydroxide, monohydrate → 4-[2-(4-Cyclobutylmethyl-piperazin-1-yl)-2-oxo-ethyl]-3-methyl-benzoic Acid

HRID 220932Notes

Reaction equation

HRID 220932 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:28])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH:23]3[CH2:26][CH2:25][CH2:24]3)[CH2:18][CH2:17]2)=[O:15])=[C:9]([CH3:27])[CH:8]=1>C1COCC1.O>[CH:23]1([CH2:22][N:19]2[CH2:18][CH2:17][N:16]([C:14](=[O:15])[CH2:13][C:10]3[CH:11]=[CH:12][C:7]([C:6]([OH:28])=[O:5])=[CH:8][C:9]=3[CH3:27])[CH2:21][CH2:20]2)[CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 575552254-[2-(4-Cyclobutylmethyl-piperazin-1-yl)-2-oxo-ethyl]-3-methyl-benzoic Acid Methyl Ester

Product 1

HCID 575554124-[2-(4-Cyclobutylmethyl-piperazin-1-yl)-2-oxo-ethyl]-3-methyl-benzoic AcidYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (122 mg, 2.9 mmol) was added to a solution of 4-[2-(4-cyclobutylmethyl-piperazin-1-yl)-2-oxo-ethyl]-3-methyl-benzoic acid methyl ester from Example E85.1 (500 mg, 1.4 mmol) in THF (10 ml) and water (5 ml). The mixture was stirred for 20 h at room temperature and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 3% acetic acid:7% methanol:90% chloroform) to yield the title compound (300 mg, 63%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash chromatography on silica gel (eluant; 3% acetic acid:7% methanol:90% chloroform)

Sources & evidence

ORD record
ord-cdf053a954fb4f2fa41815fc66857815
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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