Lithium hydroxide, monohydrate → 3-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-acrylic Acid

HRID 11660Notes

Reaction equation

HRID 11660 reaction equation
C[O:2][C:3](=[O:33])[CH:4]=[CH:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[O:13][CH2:14][C:15]([N:17]1[CH2:22][C@H:21]([CH3:23])[N:20]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:19][C@H:18]1[CH3:32])=[O:16].O.[OH-].[Li+]>O1CCCC1.CO.O>[Cl:12][C:10]1[CH:9]=[CH:8][C:7]([O:13][CH2:14][C:15]([N:17]2[CH2:22][C@H:21]([CH3:23])[N:20]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[CH2:19][C@H:18]2[CH3:32])=[O:16])=[C:6]([CH:5]=[CH:4][C:3]([OH:33])=[O:2])[CH:11]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 696556013-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-acrylic acid methyl ester

Product 1

HCID 692968183-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-acrylic Acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-acrylic acid methyl ester (0.060 g, 0.13 mmol) in tetrahydrofuran, methanol and water (1 ml each) was added lithium hydroxide hydrate (0.020 g, 0.51 mmol). After 1 hour at 50° C. the reaction was concentrated and the title compound was isolated by chromatography on silica gel (0.032 g, LRMS: 461.1).

Workup

  1. concentrationAfter 1 hour at 50° C. the reaction was concentrated

Sources & evidence

ORD record
ord-be6ad7bc3d474d659900cfee4abc1226
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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