Ethyl Acetate → 2-(N-allyloxycarbonylaminomethyl)-3-(t-butyldimethylsilyloxy)butylamine
Reaktionsgleichung
[CH2:1]([O:4][C:5]([NH:7][CH2:8][CH:9]([CH:16]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH3:17])[CH2:10]OS(C)(=O)=O)=[O:6])[CH:2]=[CH2:3].[Cl-].[NH4+].[N-:28]=[N+]=[N-].[Na+].C(OCC)(=O)C>CN(C)C=O.O>[CH2:1]([O:4][C:5]([NH:7][CH2:8][CH:9]([CH:16]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH3:17])[CH2:10][NH2:28])=[O:6])[CH:2]=[CH2:3]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
To a solution of 7.00 g of 2-(N-allyloxycarbonylaminomethyl)-3-t-butyldimethylsilyloxy-1-methanesulfonyloxybutane and 1.42 g of ammonium chloride in 70 ml of N,N-dimethylformamide was added 1.73 g of sodium azide at 0° C. The mixture was stirred at 50° C. for 7 hours. After the starting material disappeared, 350 ml of ethyl acetate and 350 ml of water were added to the reaction mixture. The organic layer was washed in turn with water three times and brine. The half amount of solvent was evaporated and then 5.11 g of triphenylphosphine was added thereto portionwise. After stirring overnight, 2.15 g of 28% aqueous ammonia was added and the mixture was stirred for 8 hours, and then evaporated under reduced pressure to give 11.36 g of crude 2-(N-allyloxycarbonylaminomethyl)-3-(t-butyldimethylsilyloxy)butylamine.
Aufarbeitung
- washThe organic layer was washed in turn with water three times and brine
- customThe half amount of solvent was evaporated
- addition5.11 g of triphenylphosphine was added
- stirringAfter stirring overnight
- addition2.15 g of 28% aqueous ammonia was added
- stirringthe mixture was stirred for 8 hours
- customevaporated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-be3f58fd5d2448d9b1fe5f886841c916
- Quelldatensatz
- uspto-grants-1994_02
- Patentnummer
- US05286721
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