Tetraethyl orthocarbonate → HCID 68359207, Verbindung

HRID 339880

Reaktionsgleichung

Reaktionsgleichung von HRID 339880
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([F:17])([S:13]([NH2:16])(=[O:15])=[O:14])[C:9]([OH:12])([CH3:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[CH2:18]([O:20][C:21](OCC)(OCC)OCC)[CH3:19]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([F:17])[C:9]([CH3:11])([CH3:10])[O:12][C:21]([O:20][CH2:18][CH3:19])=[N:16][S:13]2(=[O:14])=[O:15])[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 66213Tetraethyl orthocarbonateHCID 68292393HCID 68292393, Verbindung

Produkt 1

HCID 68359207HCID 68359207, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 75 mg of 1-(3-bromophenyl)-1-fluoro-2-hydroxy-2-methylpropane-1-sulfonamide in 5 ml of tetraethoxymethane and 1 ml of acetic acid was stirred at 100° C. for 1.5 hours. The conversion was checked by LCMS. Since it was incomplete, the reaction mixture was stirred at 100° C. for a further 3.5 hours. After the removal of the solvents under reduced pressure, the residue was purified by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (45.6 mg) with a molecular weight of 380.2 g/mol (C13H15BrFNO4S).

Aufarbeitung

  1. stirringthe reaction mixture was stirred at 100° C. for a further 3.5 hours
  2. customAfter the removal of the solvents under reduced pressure
  3. customthe residue was purified by means of normal phase chromatography
  4. concentrationconcentrated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-9bfd0b628c204c6d95b22f944706bc75
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895547B2

Verknüpfte Notizen

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