Methanesulfonic acid (5R)-3-(3-fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester → (5R)-2-[3-(3-fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-isoindole-1,3-dione

HRID 341137Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 341137
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14]OS(C)(=O)=O)[O:11][C:10]2=[O:20])[CH:5]=[CH:6][C:7]=1[I:8].[C:21]1(=[O:31])[NH:25][C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12.[K]>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@@H:12]([CH2:14][N:25]3[C:21](=[O:31])[C:22]4[C:23](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:24]3=[O:26])[O:11][C:10]2=[O:20])[CH:5]=[CH:6][C:7]=1[I:8]

Komponenten

4

Edukt 2

HCID 23624705Methanesulfonic acid (5R)-3-(3-fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl esterHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 66884332(5R)-2-[3-(3-fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-isoindole-1,3-dioneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution of mesylate 105 (26.38 g, 63.57 mmol) in anhydrous N,N-dimethylformamide (DMF, 120 mL) was treated with solid potassium phthalimide (12.95 g, 70.0 mmol, 1.1 equiv) at 25° C., and the resulting reaction mixture was warmed to 70° C. for 2 h. When TLC and HPLC showed the reaction was complete, the reaction mixture was cooled to room temperature before being quenched with H2O (400 mL). The resulting mixture was stirred at room temperature for 10 min before being cooled to 0-5° C. for 1 h. The white precipitate was collected by filtration, washed with water (3×100 mL), and dried in vacuo to afford the desired (5R)-2-[3-(3-fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-isoindole-1,3-dione 106 (27.85 g, 94%) as an off-white powder. This product was directly used in subsequent reactions without further purification. C18H12FIN2O4, LCMS (EI) m/e 467 (M++H).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. temperaturethe reaction mixture was cooled to room temperature
  3. custombefore being quenched with H2O (400 mL)
  4. temperaturebefore being cooled to 0-5° C. for 1 h
  5. filtrationThe white precipitate was collected by filtration
  6. washwashed with water (3×100 mL)
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c65aa68bd1c341fe92b618d6948cb9b9
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895741B2

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