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Potassium Carbonate → (5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzylsulfanyl)-acetic acid methyl ester

HRID 11692
Notes
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Reaction equation

HRID 11692 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:15][C@H:14]([CH3:16])[N:13]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:12][C@H:11]2[CH3:25])=[O:9])=[C:4]([CH2:28]Cl)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:36]([O:40][CH3:41])(=[O:39])[CH2:37][SH:38]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH3:41][O:40][C:36](=[O:39])[CH2:37][S:38][CH2:28][C:4]1[CH:3]=[C:2]([Cl:1])[CH:27]=[CH:26][C:5]=1[O:6][CH2:7][C:8]([N:10]1[CH2:15][C@H:14]([CH3:16])[N:13]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[CH2:12][C@H:11]1[CH3:25])=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 234058422-[4-Chloro-2-(chloromethyl)phenoxy]-1-{(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl}ethan-1-one

Product 1

HCID 69655783(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzylsulfanyl)-acetic acid methyl ester

Reagents, catalysts & solvents 3

HCID 67553
Tetrabutylammonium Iodide
Catalyst
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To 2-(4-chloro-2-chloromethyl-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.10 g, 0.23 mmol) in dimethyl formamide (2 ml) was added potassium carbonate (0.070 g, 0.51 mmol), tetrabutylammonium iodide (0.088 mg, 0.24 mmol) and finally methyl thioglycolate (0.02 ml, 0.25 mmol). The reaction was stirred at 50° C. for 19 hours. The reaction was diluted with ethyl acetate and washed with pH 7 phosphate buffer (0.05 M) and aqueous saturated sodium chloride. The organic layer was dried over magnesium sulfate and the title compound was isolated by chromatography on silica gel (0.046 g).

Workup

  1. washwashed with pH 7 phosphate buffer (0.05 M) and aqueous saturated sodium chloride
  2. dry with materialThe organic layer was dried over magnesium sulfate

Sources & evidence

ORD record
ord-9761802317cd43b78bc46201bd46de50
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07098212B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes