5-Chlorothiophene-2-sulfonyl isoleucinol → 5-Chloro-N-[(S,S)-1-formyl-2-methylbutyl]thiophene-2-sulfonamide
Reaktionsgleichung
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Cl:12][C:13]1[S:17][C:16]([S:18]([NH:21][C@H:22]([CH2:27][OH:28])[C@H:23]([CH2:25][CH3:26])[CH3:24])(=[O:20])=[O:19])=[CH:15][CH:14]=1>C(Cl)Cl>[Cl:12][C:13]1[S:17][C:16]([S:18]([NH:21][C@H:22]([CH:27]=[O:28])[C@@H:23]([CH3:24])[CH2:25][CH3:26])(=[O:20])=[O:19])=[CH:15][CH:14]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Molecular sieves (15 g, 4 Å) were stirred in dry CH2Cl2 (175 mL) for 10 min. Then a mixture of pyridinium chlorochromate (8.6 g, 39.9 mmol) and silica gel (9 g) was added and the mixture was stirred an additional 10 min. To the suspension was added 5-chlorothiophene-2-sulfonyl isoleucinol (4 g, 13.4 mmol) dissolved in CH2Cl2 (15 mL) and the resulting slurry was stirred for 2 h. The reaction mixture was filtered and the solvent was removed. The residue was subjected to a Biotage™ eluting with 20% EtOAc/hexane to give 3.22 g (81%) of the aldehyde (LCMS=294.21 (M−H), rt=1.10 min).