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

HRID 1351305Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1351305
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ec79ccc84e914daa821fdbb156d063a9
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07217723B2

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