Water → 5-(S)-Acetamidomethyl-3-[4'-triphenylmethylthio-3'-fluorophenyl]oxazolidine-2-one

HRID 2305647Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2305647
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH2:23][C@H:24]1[O:28][C:27](=[O:29])[N:26]([C:30]2[CH:35]=[CH:34][C:33]([S:36][C:37]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[C:32]([F:56])[CH:31]=2)[CH2:25]1)=[N+]=[N-].O.[C:58](OC(=O)C)(=[O:60])[CH3:59].N1C=CC=CC=1>C1COCC1>[C:58]([NH:20][CH2:23][C@@H:24]1[O:28][C:27](=[O:29])[N:26]([C:30]2[CH:35]=[CH:34][C:33]([S:36][C:37]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[C:32]([F:56])[CH:31]=2)[CH2:25]1)(=[O:60])[CH3:59]

Komponenten

7

Edukt 5

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 11776TriphenylphosphineHCID 229662215-(S)-azidomethyl-3-[4'-triphenylmethylthio-3'-fluorophenyl]-oxazolidine-2-one

Produkt 1

HCID 229661975-(S)-Acetamidomethyl-3-[4'-triphenylmethylthio-3'-fluorophenyl]oxazolidine-2-oneAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triphenylphosphine (2.82 g, 10.8 mmol) was added portionwise to a solution of 5-(S)-azidomethyl-3-[4′-triphenylmethylthio-3′-fluorophenyl]oxazolidine-2-one (5.00 g, 9.79 mmol) in THF (40 mL), and the mixture stirred for 2 h at room temperature. Water (1.41 mL, 78.3 mmol) was added, and the mixture heated at 40° C. overnight. Solvent was removed under vacuum, and the oily residue dissolved in dichloromethane (50 mL). Acetic anhydride (4.62 ml, 49.0 mmol) and pyridine (7.92 ml, 97.9 mmol) were added, and the mixture stirred for 8 h at r.t. Solvent was removed under vacuum and the crude product purified by silica gel flash column chromatography (eluent: 30% ethyl acetate in hexanes) to give the product as a foam (4.98 g, 97%); MS (m/z): [M+H]+=527.

Aufarbeitung

  1. temperaturethe mixture heated at 40° C. overnight
  2. customSolvent was removed under vacuum
  3. dissolutionthe oily residue dissolved in dichloromethane (50 mL)
  4. stirringthe mixture stirred for 8 h at r.t
  5. customSolvent was removed under vacuum
  6. customthe crude product purified by silica gel flash column chromatography (eluent: 30% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-38b085f7bd6446be890674c0c6d12eb0
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06441005B1

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