Z-Asn-OtBu → L-Asparagine tert-butyl ester
Reaktionsgleichung
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5]>C(OCC)(=O)C.[C].[Pd]>[NH2:1][C@H:2]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
23.6 Grams (73.2 mmols) of Z-Asn-OtBu in 200 ml of ethyl acetate are hydrogenated in the presence of 2 g of palladium carbon (10% Pd) until, after 1 hour, hydrogen is no longer absorbed. The catalyst is filtered off and the filtrate concentrated, whereupon the product, melting at 96°-98° C., crystallizes out. Optical rotation [α]D20 =+2° (c=2.1 in methanol). In the thin-layer chromatogram on silica gel the Rf52 =0.30; Rf45 =0.50.