Water → tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-(3-hydroxypent-1,4-dien-3-yl)-1,4-oxazepane-4-carboxylate
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:15]([C:16](OC)=[O:17])[O:14][CH2:13][CH2:12][N:11]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:27]([Mg]Br)=[CH2:28].[CH2:31]1COC[CH2:32]1.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:15]([C:16]([OH:17])([CH:27]=[CH2:28])[CH:31]=[CH2:32])[O:14][CH2:13][CH2:12][N:11]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of 4-tert-butyl 7-methyl (6R,7R)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4,7-dicarboxylate (2.86 g) in THF (30 mL) was added 1.0 M vinylmagnesium bromide/THF solution (15.6 ml) under ice-cooling. The mixture was stirred at 0° C. for 20 min under nitrogen purging, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-50%)) to give the title compound (2.31 g) as a colorless oil.
Aufarbeitung
- temperaturecooling
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated
- customThe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-50%))
Quellen und Nachweise
- ORD-Eintrag
- ord-1382898bd28248b1a729ee2155e8deaf
- Quelldatensatz
- uspto-grants-2014_05
- Patentnummer
- US08722662B2
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