Sodium hydride → (+)-3-(3,4-Difluorophenyl)-5-oxo-morpholine-4-carboxylic acid-4-nitro-phenyl ester

HRID 1860399Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1860399
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[NH:14][C:13](=[O:15])[CH2:12][O:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[H-].[Na+].Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1)=[O:20]>C1COCC1>[N+:28]([C:25]1[CH:24]=[CH:23][C:22]([O:21][C:19]([N:14]2[C:13](=[O:15])[CH2:12][O:11][CH2:10][CH:9]2[C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)=[O:20])=[CH:27][CH:26]=1)([O-:30])=[O:29]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 821294-Nitrophenyl chloroformateHCID 18623221HCID 18623221, Verbindung

Produkt 1

HCID 15550626(+)-3-(3,4-Difluorophenyl)-5-oxo-morpholine-4-carboxylic acid-4-nitro-phenyl esterAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 5-(3,4-difluoro-phenyl)-morpholin-3-one (0.34 g, 1.57 mmol) in 10 mL of THF was added NaH (0.05 g, 1.9 mmol) and the resulting solution was stirred for 30 min. It was then transferred via a syringe into a solution of 4-nitrophenyl chloroformate in 20 mL of anhydrous THF at −78° C. under argon. The resulting solution was stirred for 2 hours after which the solvent was removed and the residue was purified by column chromatography on silica gel with 1:1 hexane/CH2Cl2 followed by CH2Cl2 to obtain 3-(3,4-difluorophenyl)-5-oxo-morpholine-4-carboxylic acid-4-nitro-phenyl ester as a colorless thick oil (0.31 g, 51%).

Aufarbeitung

  1. stirringThe resulting solution was stirred for 2 hours after which the solvent
  2. customwas removed
  3. customthe residue was purified by column chromatography on silica gel with 1:1 hexane/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-20c1f9364dac4068948f7f0b01240925
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531471B2

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