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Triethylamine → (5-[1-(t-Butyldimethylsiloxy)vinyl]-3-{[2-(4-fluorophenyl)ethyl]-methylsulfamoyl}thiophene-2-yl)carbamic acid t-butyl ester

HRID 1351316
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1351316
[C:1]([O:5][C:6](=[O:30])[NH:7][C:8]1[S:9][C:10]([C:27](=[O:29])[CH3:28])=[CH:11][C:12]=1[S:13](=[O:26])(=[O:25])[N:14]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[CH3:15])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Si:38](OS(C(F)(F)F)(=O)=O)([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39].C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([O:5][C:6](=[O:30])[NH:7][C:8]1[S:9][C:10]([C:27]([O:29][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])=[CH2:28])=[CH:11][C:12]=1[S:13](=[O:25])(=[O:26])[N:14]([CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=1)[CH3:15])([CH3:4])([CH3:2])[CH3:3]
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Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 69414947(5-Acetyl-3-{[2-(4-fluorophenyl)ethyl]methylsulfamoyl}thiophene-2-yl)-carbamic acid t-butyl ester

Produkt 1

HCID 69415031(5-[1-(t-Butyldimethylsiloxy)vinyl]-3-{[2-(4-fluorophenyl)ethyl]-methylsulfamoyl}thiophene-2-yl)carbamic acid t-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (5-acetyl-3-{[2-(4-fluorophenyl)ethyl]methylsulfamoyl}thiophene-2-yl)-carbamic acid t-butyl ester (the compound of Preparation Example 111) (946 mg) in dichloromethane (8 mL) was added triethylamine (0.58 mL) and 0.71 mL of t-butyldimethylsilyltrifluoromethane sulfonate (0.71 mL) on an ice bath. After stirring for 30 minutes, an aqueous solution of saturated sodium bicarbonate 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 removal of the solvent by evaporation was purified by silica gel column chromatography (hexane/ethyl acetate) and, the title compound (985 mg) was obtained as a colorless oily matter.

Aufarbeitung

  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 upon removal of the solvent by evaporation
  4. customwas purified by silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-ee232449073445d9ad25b1a320fd3590
Quelldatensatz
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07217723B2

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