Sodium Azide → (3S,5S)-5-[(S)-1-Azido-2-benzyloxyethyl]-3-isopropyldihydrofuran-2-one
Reaktionsgleichung
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:12][CH2:13][C@H:14]([C@H:16]1[O:20][C:19](=[O:21])[C@H:18]([CH:22]([CH3:24])[CH3:23])[CH2:17]1)Br)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CN1C(=O)N(C)CCC1>[N:1]([C@H:14]([C@H:16]1[O:20][C:19](=[O:21])[C@H:18]([CH:22]([CH3:24])[CH3:23])[CH2:17]1)[CH2:13][O:12][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[N+:2]=[N-:3]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 40 °C
Versuchsvorschrift
5.10 g of sodium azide (78.5 mmol) was added to a solution of 22.33 g of (3S,5S)-5-[(1R)-2-benzyloxy-1-bromoethyl]-3-isopropyldihydrofuran-2-one obtained in Example (1d) (65.4 mmol) in N,N′-dimethylpropyleneurea (130 ml) at room temperature, and the mixture was stirred at 40° C. for three days. The reaction mixture was cooled and then poured into ice water, followed by extraction with diethyl ether. Then, the organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=6/1) to obtain 10.19 g of the title compound (yield: 51%).
Aufarbeitung
- temperatureThe reaction mixture was cooled
- extractionfollowed by extraction with diethyl ether
- washThen, the organic layer was washed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationAfter filtration
- customthe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=6/1)
Quellen und Nachweise
- ORD-Eintrag
- ord-94aca53dc13a447c857faf9c558ba6ed
- Quelldatensatz
- uspto-grants-2012_04
- Patentnummer
- US08158790B2
Notizen zur Reaktion
Wird geladen…