Reaktionsgleichung
[F:1][CH2:2][CH2:3][O:4][CH2:5][C@@H:6]1[CH2:10][C@@H:9](OS(C)(=O)=O)[CH2:8][N:7]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)=[O:17].[C:29]([SH:32])(=[O:31])[CH3:30].CC(C)([O-])C.[K+]>CN(C)C=O>[C:29]([S:32][C@@H:9]1[CH2:8][N:7]([C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=2)=[O:17])[C@H:6]([CH2:5][O:4][CH2:3][CH2:2][F:1])[CH2:10]1)(=[O:31])[CH3:30]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of (2S,4R)-2-(2-fluoroethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (4.95 g) in dimethylformamide (5 ml) was added to a mixture of thioacetic S-acid (1.26 ml) and potassium tert-butoxide (1.98 g) in dimethylformamide (25 ml) in a nitrogen stream, and the mixture was heated at 75°-80° C. for 2 hours. The mixture was poured into ice-water (100 ml) and extracted with ethyl acetate (100 ml). The extract was washed with water (100 ml×2) and brine (100 ml), in turn, dried over magnesium sulfate, and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (80 g) and eluted with chloroform to give (2S,4S)-4-acetylthio-2-(2-fluoroethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.75 g).
Aufarbeitung
- temperaturethe mixture was heated at 75°-80° C. for 2 hours
- extractionextracted with ethyl acetate (100 ml)
- washThe extract was washed with water (100 ml×2) and brine (100 ml), in turn
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customto give a syrup
- washeluted with chloroform
Quellen und Nachweise
- ORD-Eintrag
- ord-561050ac5e184cdba136ada41a18f756
- Quelldatensatz
- uspto-grants-1991_01
- Patentnummer
- US04983596
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