Thiophenol → N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]glycine methyl ester

HRID 2303354Notes

Reaction equation

HRID 2303354 reaction equation
[CH3:1][O:2][C:3](=[O:37])[CH2:4][N:5](S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=2)[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].C1(S)C=CC=CC=1.C(OCC)(=O)C>C(#N)C>[CH3:1][O:2][C:3](=[O:37])[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([C:13]2[CH:14]=[C:15]([O:23][CH3:24])[C:16]([O:21][CH3:22])=[C:17]([O:19][CH3:20])[CH:18]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 18460573N-(2-nitrobenzenesulfonyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]glycine methyl ester

Product 1

HCID 18460587N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]glycine methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(2-Nitrobenzenesulfonyl)-N-[[2-(3,4,5-trimethoxy-phenyl)pyridin-4-yl]methyl]glycine methyl ester (11.35 g) was dissolved in acetonitrile (30 mL), and to the solution potassium carbonate (3.39 g) was added. Thiophenol (2.37 g) was then added to the mixture, and the resultant mixture was stirred overnight at room temperature. Ethyl acetate was added to the reaction mixture, and the resultant mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was then purified by column chromatography on silica gel (chloroform:methanol=20:1) to obtain the title compound.

Workup

  1. washthe resultant mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was then purified by column chromatography on silica gel (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-665b83372ca549919c23d655afc32728
Source dataset
uspto-grants-2002_08
Patent number
US06432957B1

Reaction notes

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