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Ethyl trifluoromethanesulphonate → (4R,5S)-[(S)-2-(2,4-Difluoro-benzyl)-butyryl]-4-methyl-5-phenyl-oxazolidin-2-one

HRID 132636
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 132636
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]([N:13]1[C@H:17]([CH3:18])[C@H:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:15][C:14]1=[O:25])=[O:12].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].O([CH2:44][CH3:45])S(C(F)(F)F)(=O)=O>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C@H:10]([CH2:44][CH3:45])[C:11]([N:13]1[C@H:17]([CH3:18])[C@H:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:15][C:14]1=[O:25])=[O:12]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 67924Ethyl trifluoromethanesulphonateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 69267110(4R,5S)-3-[3-(2,4-Difluoro-phenyl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one

Produkt 1

HCID 69267273(4R,5S)-[(S)-2-(2,4-Difluoro-benzyl)-butyryl]-4-methyl-5-phenyl-oxazolidin-2-oneAusbeute 50,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A flask was charged with 54 g (156 mmol) of (4R,5S)-3-[3-(2,4-difluoro-phenyl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one and 300 mL of dry THF, and the solution was cooled to −78° C. To this solution was added 172 mL (172 mmol) of 1 M NaHMDS in THF, and the mixture was stirred cold for 1 hour. Then 30.6 g (172 mmol) of ethyl triflate was added dropwise to the enolate solution, and the reaction mixture was warmed to −40° C. to −30° C. and stirred for 1.5 hours. The reaction mixture was quenched by the addition of aqueous brine. The THF was removed under reduced pressure and the residue was partitioned between EtOAc and water. The organics were collected, and EtOAc was removed under reduced pressure. The resulting crude oil was purified by column chromatography (3:1 hexanes/EtOAc eluent) to get 29.5 g of an impure oil that was used without further purification.

Aufarbeitung

  1. temperaturethe reaction mixture was warmed to −40° C. to −30° C.
  2. stirringstirred for 1.5 hours
  3. customThe reaction mixture was quenched by the addition of aqueous brine
  4. customThe THF was removed under reduced pressure
  5. customthe residue was partitioned between EtOAc and water
  6. customThe organics were collected
  7. customEtOAc was removed under reduced pressure
  8. customThe resulting crude oil was purified by column chromatography (3:1 hexanes/EtOAc eluent)

Quellen und Nachweise

ORD-Eintrag
ord-1283cdf6e9494f07a7fa75b0cc0ec495
Quelldatensatz
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07388023B2

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