Tetrahydrofuran → p-Nitrobenzyl (4-tert-butylthio-2-oxo-1-azetidinyl)acetate
Reaktionsgleichung
C[Si]([N-:5][Si](C)(C)C)(C)C.[Li+].[C:11]([S:15]N1CCC1=O)([CH3:14])([CH3:13])[CH3:12].Br[CH2:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:24].[O:36]1C[CH2:39][CH2:38][CH2:37]1>CN(C)C=O>[C:11]([S:15][CH:39]1[N:5]([CH2:22][C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])[C:37](=[O:36])[CH2:38]1)([CH3:14])([CH3:13])[CH3:12]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -30 °C
Versuchsvorschrift
14.4 ml of 1 N solution of lithium bis-trimethylsilylamide in tetrahydrofuran (THF) are added dropwise with stirring at -70° C. to a solution of 1.91 g (12 mmol) of tert-butylthioazetidin-2-one in 6 ml of dry N,N-dimethylformamide (DMF) and then a solution of 4.93 g (18 mmol) of p-nitrobenzyl bromoacetate in 6 ml of DMF is added dropwise to the mixture and the mixture is stirred at -30° C. for a further 30 minutes. Dilution of the reaction mixture with 100 ml of toluene, washing with three portions of 50 ml each of water, drying the organic phase over magnesium sulphate and evaporating the solvent in vacuo yields 4.3 g of solid crude product, which is chromatographed on 120 g of silica gel using toluene/ethyl acetate (4:1). The purified product (2.6 g) is recrystallized from 100 ml of dry isopropanol.
Aufarbeitung
- washDilution of the reaction mixture with 100 ml of toluene, washing with three portions of 50 ml each of water
- dry with materialdrying the organic phase over magnesium sulphate
- customevaporating the solvent in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-39555710e1bc46829693a0f4ad1f1377
- Quelldatensatz
- uspto-grants-1992_04
- Patentnummer
- US05108747
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