Methanesulfonyl chloride → (5R)-3-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-ylmethyl methanesulfonate

HRID 8159

Reaktionsgleichung

Reaktionsgleichung von HRID 8159
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][OH:20])[O:16][C:15]2=[O:21])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1.C(N(CC)CC)C>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][O:20][S:23]([CH3:22])(=[O:25])=[O:24])[O:16][C:15]2=[O:21])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]1

Komponenten

5

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 21356561(5R)-3-(3-Fluoro-4-(4-methylimidazol-1-yl)phenyl)-5-hydroxymethyloxazolidin-2-one

Produkt 1

HCID 21356562(5R)-3-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-ylmethyl methanesulfonateAusbeute 78,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

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°.

Aufarbeitung

  1. customSolvent was evaporated
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. dry with materialisohexane, and dried
  5. customThe residue was recrystallised from hot acetone (200 ml) by dilution with isohexane (300 ml)

Quellen und Nachweise

ORD-Eintrag
ord-2f379275646448efaafdb55402752361
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087629B2

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