Methyl iodide → 6-(4-(2-(N-Methyl-4-chlorobenzenesulphonylamino)ethyl)phenyl)-6-(3-pyridyl)hex-5-enoic acid

HRID 487331

Reaction equation

HRID 487331 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[CH:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:16][CH:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:34](Cl)Cl.CI>[OH-].[Na+].[Cl-].C([N+](C)(C)C)C1C=CC=CC=1>[CH3:34][N:11]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:9])=[O:10])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[CH:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 659716-(4-(2-(4-Chlorobenzenesulphonylamino)ethyl)-phenyl)-6-(3-pyridyl)hex-5-enoic acid

Product 1

HCID 542628046-(4-(2-(N-Methyl-4-chlorobenzenesulphonylamino)ethyl)phenyl)-6-(3-pyridyl)hex-5-enoic acid

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

2.0 g of 6-(4-(2-(4-chlorobenzenesulphonylamino)ethyl)-phenyl)-6-(3-pyridyl)hex-5-enoic acid are stirred overnight in 10 ml of 4N sodium hydroxide solution, 100 ml of methylene chloride, 80 mg of benzyl trimethylammonium chloride and 0.85 g of methyl iodide. Then the organic phase is separated off and the aqueous phase is acidified to pH 5. The product precipitated is separated off and taken up in methylene chloride, dried and evaporated down. Finally, the residue is chromatographed with ethylene chloride/methanol (97:3) over a silica gel column.

Workup

  1. customThen the organic phase is separated off
  2. customThe product precipitated
  3. customis separated off
  4. customdried
  5. customevaporated down
  6. customFinally, the residue is chromatographed with ethylene chloride/methanol (97:3) over a silica gel column

Sources & evidence

ORD record
ord-5bd35299ab28429799ed76c9d3dd6466
Source dataset
uspto-grants-1994_03
Patent number
US05294626

Linked notes

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