Nitrogen → HCID 66917466, compound

HRID 2355209Notes

Reaction equation

HRID 2355209 reaction equation
[CH3:1][O:2][C:3](=[O:22])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:8][C:7]=1[Br:21].N#N>O=[Pt]=O.CCO.C1COCC1>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)(=[O:14])=[O:13])=[CH:8][C:7]=1[Br:21]

Participants

5

Reactant 2

HCID 947NitrogenHCID 66917477HCID 66917477, compound

Product 1

HCID 66917466HCID 66917466, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of (E)-3-(4-benzenesulfonyl-2-bromo-phenyl)-acrylic acid methyl ester (8.52 g) in a mixture EtOH/THF (2/1, 150 mL) was added under N2 atmosphere PtO2 (0.45 g). A balloon filled with H2 was set up and N2 was replaced with H2, the reaction was then stirred for 4 h 30 min. The mixture was filtered and the filtrate was evaporated in vacuo. The residue was purified via flash chromatography (hexane/EtOAc, 85/15) affording 3-(4-benzenesulfonyl-2-bromo-phenyl)-propionic acid methyl ester (6.73 g).

Workup

  1. additionA balloon filled with H2
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified via flash chromatography (hexane/EtOAc, 85/15)

Sources & evidence

ORD record
ord-bdd9ee0a2ffd439fa1ba609b68eb2721
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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