Cesium carbonate → Isohexane ethyl acetate

HRID 1443997Notes

Reaction equation

HRID 1443997 reaction equation
Br[C:2]1[N:3]=[C:4]([O:28][CH3:29])[C:5]([N:8](COCC[Si](C)(C)C)[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])(=[O:11])=[O:10])=[N:6][CH:7]=1.[CH3:30][O:31][C:32](=[O:35])[CH2:33][SH:34].[C:36](=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.ClCCl>[C:32]([O:31][CH2:30][CH3:2])(=[O:35])[CH3:33].[CH3:12][CH2:17][CH2:16][CH:15]([CH3:14])[CH3:36].[Cl:19][C:13]1[C:14]([Cl:18])=[CH:15][CH:16]=[CH:17][C:12]=1[S:9]([NH:8][C:5]1[N:6]=[CH:7][C:2]([S:34][CH2:33][C:32]([OH:35])=[O:31])=[N:3][C:4]=1[O:28][CH3:29])(=[O:10])=[O:11]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 16907Methyl ThioglycolateHCID 59168156N-(5-Bromo-3-methoxy-2-pyrazinyl)-2,3-dichloro-N-[{2-(trimethylsilanyl)ethoxy}methyl]benzenesulphonamide

Product 2

HCID 21882781Isohexane ethyl acetateHCID 59168222[5-(2,3-Dichlorobenzenesulphonylamino)-6-methoxy-2-pyrazinylsulphanyl]acetic acid

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

N-(5-Bromo-3-methoxy-2-pyrazinyl)-2,3-dichloro-N-[{2-(trimethylsilanyl)ethoxy}methyl]benzenesulphonamide (0.40 g), mercaptoacetic acid methyl ester (0.1 g) and caesium carbonate (0.6 g) in acetonitril (10 mL) was stirred at room temperature. After 16 h, the solution was diluted with dichloromethane, filtered and evaporated. Chromatography on silica gel eluting with ethyl acetate/isohexane mixtures gave the title compound with SEM group attached. The compound was dissolved in trifluoroacetic acid (5mL). After 2 h, toluene (20 mL) was added and the solution evaporated. Chromatography on silica gel eluting with ethyl acetate/isohexane mixtures gave the title compound as a white solid (0.15 g).

Workup

  1. filtrationfiltered
  2. customevaporated

Sources & evidence

ORD record
ord-46cfcfc59bf34673946f4faaf5e7fc76
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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