2-(3-Bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid methyl ester → HCID 12069498, compound

HRID 430271Notes

Reaction equation

HRID 430271 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[C:13](Br)[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[Cu][C:24]#[N:25]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:22])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[C:13]([C:24]#[N:25])[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 120676652-(3-Bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid methyl esterHCID 178418546HCID 178418546, compound

Product 1

HCID 12069498HCID 12069498, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2-(3-bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid methyl ester (990.0 mg, 2.54 mmol) and copper(I) cyanide (273.3 m g, 3.05 mmol) in dry N,N-dimethylformamide (2.5 mL) was heated under reflux for 4 h. The reaction was allowed to cool to 25° C., and the crude reaction mixture was directly purified without further chemical work-up. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 100% hexanes then 3/1 hexanes/ethyl acetate) afforded 2-(3-cyano-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid methyl ester (646.5 mg, 76%) as a very light yellow oil: EI-HRMS m/e calcd for C17H21NO4S (M+) 335.1191, found 335.1185.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. customthe crude reaction mixture
  4. customwas directly purified without further chemical work-up

Sources & evidence

ORD record
ord-1bef1f2db04744e9a207f8cba45ce106
Source dataset
uspto-grants-2001_11
Patent number
US06320050B1

Reaction notes

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