Ethyl bromoacetate → [4-(4'-Trifluoromethylbiphenyl-2-carbonylamino)piperidin-1-yl]acetic acid ethyl ester

HRID 494403

Reaction equation

[F:1][C:2]([F:25])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]([NH:17][CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:32]([O:34][C:35](=[O:38])[CH2:36]Br)[CH3:33]>CN(C)C=O>[CH2:32]([O:34][C:35](=[O:38])[CH2:36][N:21]1[CH2:20][CH2:19][CH:18]([NH:17][C:15]([C:10]2[C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:24])[F:25])=[CH:8][CH:7]=3)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:16])[CH2:23][CH2:22]1)[CH3:33]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4-(4′-trifluoromethylbiphenyl-2-carbonylamino)piperidine (1.03 g) obtained in Example 8b) in dimethylformamide (5 mL) were added potassium carbonate (276 mg) and bromoacetic acid ethyl ester (223 μL). The mixture was stirred overnight at ambient temperature of 90° C., and then concentrated in vacuo. The residue was distributed with water and chloroform, and the aqueous layer was further extracted with chloroform. The organic layers were combined, washed with saturated brine, dried over sodium sulfate, concentrated in vacuo and purified by column chromatography on silica gel with chloroform:methanol=30:1 to give the title compound (598 mg).

Workup

concentrationconcentrated in vacuo
extractionthe aqueous layer was further extracted with chloroform
washwashed with saturated brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
custompurified by column chromatography on silica gel with chloroform

Sources & evidence

ORD record: ord-6f2ce5d29b81410d8be4796435f060ef
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538140B2

Linked notes

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