Reaktion #8255

Reaktionsgleichung

3-(3-Fluoro-4-(4-methylimidazol-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one

Methanesulfonyl chloride

→

title product

Ausbeute 78.2%

3-(3-fluoro-4-(4-methylimidazol-1-yl)phenyl)-5(R)-methanesulfonyloxymethyloxazolidin-2-one

Ausbeute 78.2%

Lösungsmittel

pyridine

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeSolvent was evaporated
2. 2
   FiltrationThe precipitate was filtered
3. 3
   Waschenwashed with water
4. 4
   Trocknenisohexane, and dried
5. 5
   SonstigeThe residue was recrystallised from hot acetone (200 ml) by dilution with isohexane (300 ml)

Vorschrift

3-(3-Fluoro-4-(4-methylimidazol-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one (11.8 g, 40.5 mM) was stirred in a mixture of pyridine (200 ml) and triethylamine (4.86 g, 48.2 mM) under nitrogen in an ice-bath. Methanesulfonyl chloride (5.16 g, 45 mM) was added dropwise, and the mixture stirrd for 2 hours, allowing the temperature to rise to ambient. Solvent was evaporated, and the residue stirred vigorously with a mixture of aqueous sodium bicarbonate (5%, 200 ml) and isohexane (200 ml). The precipitate was filtered, washed with water then isohexane, and dried. The residue was recrystallised from hot acetone (200 ml) by dilution with isohexane (300 ml) to give the title product (11.7 g), mp 151–153°.

Quelle