Tetrahydrofuran → [(5-Chloro-2-{2-[4-(4-Fluoro-Benzyl)-(2R,5S)-2,5-Dimethyl-Piperazin-1-Yl]-2-Oxo-Ethoxy}-Benzyl)-Methyl-Amino]-Acetic Acid

HRID 11701Notes

Reaction equation

HRID 11701 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][N:5]([CH2:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[O:15][CH2:16][C:17]([N:19]1[CH2:24][C@H:23]([CH3:25])[N:22]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH2:21][C@H:20]1[CH3:34])=[O:18])[CH3:6].O1CCCC1.O.[OH-].[Li+]>O>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]([O:15][CH2:16][C:17]([N:19]2[CH2:24][C@H:23]([CH3:25])[N:22]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)[CH2:21][C@H:20]2[CH3:34])=[O:18])=[C:8]([CH:13]=1)[CH2:7][N:5]([CH2:4][C:3]([OH:35])=[O:2])[CH3:6]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 69655231[(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyl)-methyl-amino]-acetic Acid Methyl Ester

Product 1

HCID 69655348[(5-Chloro-2-{2-[4-(4-Fluoro-Benzyl)-(2R,5S)-2,5-Dimethyl-Piperazin-1-Yl]-2-Oxo-Ethoxy}-Benzyl)-Methyl-Amino]-Acetic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of [(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyl)-methyl-amino]-acetic acid methyl ester (0.051 g, 0.10 mmol) in 1:1 tetrahydrofuran:water (1 ml) and lithium hydroxide hydrate (0.016 g, 0.38 mmol) was added. After 1.5 hours the reaction was concentrated and the title compound isolated by chromatography on silica gel (0.045 g, LRMS: 492.4).

Workup

  1. concentrationAfter 1.5 hours the reaction was concentrated

Sources & evidence

ORD record
ord-d9dbec4460ec4cf99a7a04f0d618dcce
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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