Potassium Cyanide → tert-butyl (6R,7R)-6-(cyanomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate
Reaktionsgleichung
[C-:1]#[N:2].[K+].[Cl:4][C:5]1[CH:6]=[C:7]([C@@H:12]2[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][C@H:13]2[CH2:26]OS(C)(=O)=O)[CH:8]=[CH:9][C:10]=1[Cl:11].C(=O)([O-])O.[Na+]>CN(C=O)C>[C:1]([CH2:26][C@H:13]1[C@H:12]([C:7]2[CH:8]=[CH:9][C:10]([Cl:11])=[C:5]([Cl:4])[CH:6]=2)[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[CH2:14]1)#[N:2]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
Potassium cyanide (1.720 g) was added to a solution of tert-butyl (6S,7R)-7-(3,4-dichlorophenyl)-6-{[(methylsulfonyl)oxy]methyl}-1,4-oxazepane-4-carboxylate (3 g) in DMF (30 ml), and the mixture was stirred at 80° C. overnight. To the reaction mixture was added aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (2.00 g).
Aufarbeitung
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-08b5932f985c4639b3fbf19496c224fe
- Quelldatensatz
- uspto-grants-2014_05
- Patentnummer
- US08722662B2
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