Sodium Azide → (5R)-5-(Azidomethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one

HRID 2066808

Reaktionsgleichung

Reaktionsgleichung von HRID 2066808
Cl[CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][N:10]=2)[CH2:4]1.[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C)C=O.O>[N:16]([CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][N:10]=2)[CH2:4]1)=[N+:17]=[N-:18]

Komponenten

5

Edukt 2

HCID 33557Sodium AzideHCID 59409863(5R)-5-(chloromethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one2×

Produkt 1

HCID 59409901(5R)-5-(Azidomethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-oneAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of (5R)-5-(chloromethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one (2.32 g, INTERMEDIATE 7) and sodium azide (1.22 g) was heated to 100° C. in 75 ml of dimethylformamide for 15 h. The mixture was then diluted with 500 ml of water and extracted with 500 ml of ethyl acetate (3×). The combined organic layers were washed with water (250 ml) and brine (250 ml). They were then dried over sodium sulfate and concentrated in vacuo to provide 2.22 g (93%) of the title compound in >95% purity via LC/MS. Mass spectrum (ESI) 254.1 (M+1).

Aufarbeitung

  1. extractionextracted with 500 ml of ethyl acetate (3×)
  2. washThe combined organic layers were washed with water (250 ml) and brine (250 ml)
  3. dry with materialThey were then dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-45672aaf143449068956c50a354f27d4
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293721B2

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