N-Boc-p-toluenesulfonamide → tert-Butyl methyl(tosyl)carbamate
Reaktionsgleichung
[CH3:1]COC(/N=N/C(OCC)=O)=O.[C:13]([NH:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)(=[O:23])=[O:22])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>CO>[CH3:1][N:20]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[S:21]([C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)(=[O:23])=[O:22]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
The crude fluorous DEAD reagent 22 was then used in Mitsunobu reactions with N-Boc-p-toluenesulfonamide. Once again, the standard mode of addition gave complete conversion with MeOH and the product, N-methyl-N-boc-p-toluenesulfonamide was isolated in 85% yield after FSPE. However, the allyl alcohol gave only trace conversion of the starting material. The organic fraction after FSPE was mostly starting material. These results are summarized in Table 7.