Dichloromethane → HCID 71238589, Verbindung

HRID 926039

Reaktionsgleichung

Reaktionsgleichung von HRID 926039
Cl.[NH2:2][C:3]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]1.C(N(CC)CC)C.ClCCl.Cl[S:22]([C:25]1[CH:26]=[C:27]([CH:37]=[CH:38][CH:39]=1)[C:28]([O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])=[O:29])(=[O:24])=[O:23]>N1C=CC=CC=1>[CH2:9]([O:8][C:6]([C:3]1([NH:2][S:22]([C:25]2[CH:26]=[C:27]([CH:37]=[CH:38][CH:39]=2)[C:28]([O:30][CH2:31][CH2:32][Si:33]([CH3:34])([CH3:35])[CH3:36])=[O:29])(=[O:23])=[O:24])[CH2:5][CH2:4]1)=[O:7])[CH3:10]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 386203Ethyl 1-aminocyclopropane-1-carboxylate hydrochlorideHCID 866763342-(Trimethylsilyl)ethyl 3-(chlorosulfonyl)benzoate

Produkt 1

HCID 71238589HCID 71238589, VerbindungAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 774 mg of ethyl 1-aminocyclopropane-1-carboxylate hydrochloride, 1.4 mL of triethylamine, and 15 mL of dichloromethane was stirred at room temperature for 30 minutes, and 15 mL of pyridine and 1.50 g of 2-(trimethylsilyl)ethyl 3-(chlorosulfonyl)benzoate were added thereto in this order, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and to the residue was added an aqueous citric acid solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 1.80 g of 2-(trimethylsilyl)ethyl 3-{[1-(ethoxycarbonyl)cyclopropyl]sulfamoyl}benzoate as a pale yellow oily substance.

Aufarbeitung

  1. stirringby stirring at room temperature overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionto the residue was added an aqueous citric acid solution
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-3341629265ae48ab83f525048cdd5e8a
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284295B2

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