Boron trifluoride etherate → HCID 44404785, Verbindung

HRID 2084933Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2084933
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:17][CH:16]2[C:18]([O:20][CH3:21])=[O:19])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[Br:22][CH2:23][CH2:24][OH:25].B(F)(F)F.CCOCC>C(OCC)(=O)C>[CH3:21][O:20][C:18](=[O:19])[CH:16]([NH:15][S:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:1][C:2]#[C:3][CH3:4])=[CH:7][CH:8]=1)(=[O:14])=[O:13])[CH2:17][O:25][CH2:24][CH2:23][Br:22]

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 108982-BromoethanolHCID 86587129HCID 86587129, Verbindung

Produkt 1

HCID 44404785HCID 44404785, VerbindungAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 0° solution of 1-({[4-(2-butynyloxy)phenyl]sulfonyl}-2-aziridinecarboxylic acid, methyl ester (0.55 g, 1.78 mmol) in 2-bromoethanol (1.26 mL, 17.8 mmol) was dropwise added boron trifluoride etherate (0.18 mL). The mixture was stirred at 0° C. for 30 minutes and stirred at room temperature for 6 hours. The reaction was diluted with ethyl acetate. The organic layer was washed with 1N NaHCO3, water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (7:3) to obtain 0.2 g of 3-(2-bromo-ethoxy)-2-(4-[2-butynyloxy]-benzenesulfonylamino)-propionic acid methyl ester. Yield: 26%. mp 45-46° C. Electrospray Mass Spec 434.1.436.1 (M+H)+.

Aufarbeitung

  1. customTo a 0°
  2. stirringstirred at room temperature for 6 hours
  3. washThe organic layer was washed with 1N NaHCO3, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (7:3)

Quellen und Nachweise

ORD-Eintrag
ord-7b8d55859b0b477fbe5574d3815e5392
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06716833B2

Notizen zur Reaktion

Wird geladen…