Triethylamine → 3-{[2-(4-Fluorophenyl)-2-hydroxy-ethyl]-methyl-sulfamoyl}-thiophene-2-carboxylic acid methyl ester

HRID 1351305Notes

Reaction equation

HRID 1351305 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:12])[CH2:9][NH:10][CH3:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:20][O:21][C:22]([C:24]1[S:25][CH:26]=[CH:27][C:28]=1[S:29](Cl)(=[O:31])=[O:30])=[O:23].C(OCC)(=O)C>O1CCCC1>[CH3:20][O:21][C:22]([C:24]1[S:25][CH:26]=[CH:27][C:28]=1[S:29](=[O:31])(=[O:30])[N:10]([CH2:9][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[OH:12])[CH3:11])=[O:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 27367332-Thiophenecarboxylic acid, 3-(chlorosulfonyl)-, methyl esterHCID 219434071-(4-Fluorophenyl)-2-(methylamino)ethan-1-ol

Product 1

HCID 694149443-{[2-(4-Fluorophenyl)-2-hydroxy-ethyl]-methyl-sulfamoyl}-thiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-2-methylamino-ethanol (8.4 g) and triethylamine (7 mL) in tetrahydrofuran (80 mL) was added 3-chloro sulfonyl-thiophene-2-carboxylic acid methyl ester (10 g) on an ice bath over 20 minutes. The solution was brought back to room temperature and stirred for 1 hour. Ethyl acetate was added to the reaction solution, the resulting salt was removed by filtration, and solvent was evaporated at reduced pressure. The residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate), and a pale yellow oily substance (15.6 g) was obtained.

Workup

  1. customwas brought back to room temperature
  2. customthe resulting salt was removed by filtration, and solvent
  3. customwas evaporated at reduced pressure
  4. customThe residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate)
  5. customa pale yellow oily substance (15.6 g) was obtained

Sources & evidence

ORD record
ord-ec79ccc84e914daa821fdbb156d063a9
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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