Ammonium Chloride → 5-(1-Hydroxy-2-methylpropyl)thiophene-3-sulfonic acid [2-(4-fluorophenyl)ethyl]-methyl-amide

HRID 1351301Notes

Reaction equation

HRID 1351301 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH3:21])[S:11]([C:14]2[CH:18]=[C:17]([CH:19]=[O:20])[S:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.[CH:22]([Mg]Br)([CH3:24])[CH3:23].O1CCCC1.[Cl-].[NH4+]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH3:21])[S:11]([C:14]2[CH:18]=[C:17]([CH:19]([OH:20])[CH:22]([CH3:24])[CH3:23])[S:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 860714225-Formylthiophene-3-sulfonic acid [2-(4-fluorophenyl)ethyl]-methyl-amideHCID 178420663HCID 178420663, compound

Product 1

HCID 866009945-(1-Hydroxy-2-methylpropyl)thiophene-3-sulfonic acid [2-(4-fluorophenyl)ethyl]-methyl-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-formylthiophene-3-sulfonic acid [2-(4-fluorophenyl)ethyl]-methyl-amide (138 mg) in tetrahydrofuran (2 mL) was added dropwise a solution (0.25 mL) of 2.0M isopropyl magnesium bromide-tetrahydrofuran on an ice bath. After stirring for 1 hour, an aqueous solution of saturated ammonium chloride was added, and the solution was extracted with ethyl acetate. After drying the organic layer with anhydrous sodium sulfate, the residue that was obtained upon removing the solvent by evaporation was purified by silica gel column chromatography (hexane/ethyl acetate) and the title compound (57 mg) was obtained as a yellow oily substance.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. dry with materialAfter drying the organic layer with anhydrous sodium sulfate
  3. customthe residue that was obtained
  4. customupon removing the solvent
  5. customby evaporation
  6. customwas purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-96ca926655eb47df8d7ed6a88640f65f
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

Loading…