Sodium Azide → (5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-azidomethyloxazolidin-2-one

HRID 723807Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 723807
[S:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18]OS(C)(=O)=O)[O:15][C:14]3=[O:24])=[CH:9][C:8]=2[F:25])[CH2:3][CH2:2]1.[N-:26]=[N+:27]=[N-:28].[Na+]>CN(C)C=O.C(OCC)(=O)C>[S:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][N:26]=[N+:27]=[N-:28])[O:15][C:14]3=[O:24])=[CH:9][C:8]=2[F:25])[CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 33557Sodium AzideHCID 11395090Methanesulfonic acid (5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl ester

Produkt 1

HCID 11450455(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-azidomethyloxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methanesulfonic acid (5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl ester (8 g, 19.7 mmol) and sodium azide (4 g, 61.5 mmol) were heated in N,N-dimethylformamide (75 ml) at 80° C. for 2 hours. It was cooled to room temperature, diluted with ethyl acetate, washed with potassium phosphate buffer (pH 7) and with water and dried over sodium sulfate. After evaporation of the solvent the title product was obtained as a brown oil (˜7 g, crude).

Aufarbeitung

  1. washwashed with potassium phosphate buffer (pH 7) and with water
  2. dry with materialdried over sodium sulfate
  3. customAfter evaporation of the solvent the title product
  4. customwas obtained as a brown oil (˜7 g, crude)

Quellen und Nachweise

ORD-Eintrag
ord-12098b579eb74b6090a0c965e6896102
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141583B2

Notizen zur Reaktion

Wird geladen…