Triazabicyclodecene → 4-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-4-oxo-butyric Acid Ethyl Ester

HRID 11622

Reaction equation

HRID 11622 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][C@H:9]([CH3:11])[N:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:7][C@H:6]1[CH3:20])=[O:4].[CH2:21]([O:23][C:24](=[O:37])[CH2:25][CH2:26][C:27]([C:29]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=1[OH:36])=[O:28])[CH3:22].C1CN2C(=NCCC2)NC1>C(#N)C>[CH2:21]([O:23][C:24](=[O:37])[CH2:25][CH2:26][C:27]([C:29]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=1[O:36][CH2:2][C:3]([N:5]1[CH2:10][C@H:9]([CH3:11])[N:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:7][C@H:6]1[CH3:20])=[O:4])=[O:28])[CH3:22]

Participants

5

Reactant 3

HCID 79873TriazabicyclodeceneHCID 113584612-Chloro-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanoneHCID 684473744-(5-Chloro-2-hydroxy-phenyl)-4-oxo-butyric Acid Ethyl Ester

Product 1

HCID 684473824-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-4-oxo-butyric Acid Ethyl EsterYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-chloro-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.11 g, 0.36 mmol), 4-(5-chloro-2-hydroxy-phenyl)-4-oxo-butyric acid ethyl ester (0.11 g, 0.43 mmol) and 1,5,7-triazabicyclo[4,4,0]dec-5-ene bound to polystyrene crosslinked with 2% DVB (0.21 g, 0.54 mmol) in acetonitrile (1.8 mL) was stirred at ambient temperature for 12 hours. The reaction mixture was filtered through a glass frit, concentrated in vacuo and purified via flash chromatography on silica gel to give the title compound (0.084 g).

Workup

  1. filtrationThe reaction mixture was filtered through a glass frit
  2. concentrationconcentrated in vacuo
  3. custompurified via flash chromatography on silica gel

Sources & evidence

ORD record
ord-fe8e31829e854627b42103dff1a859eb
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Linked notes

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