Water → N'-(2,4,6-trimethoxybenzyl)-L-asparagine

Reaktionsgleichung

[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:20]([O:22]CC1C=CC=CC=1)=[O:21])[CH2:3][C:4](=[O:19])[NH:5][CH2:6][C:7]1[C:16]([O:17][CH3:18])=[CH:15][C:12]([O:13][CH3:14])=[CH:11][C:8]=1[O:9][CH3:10].O.CN(C=O)C>C(O)(=O)C>[CH3:18][O:17][C:16]1[CH:15]=[C:12]([O:13][CH3:14])[CH:11]=[C:8]([O:9][CH3:10])[C:7]=1[CH2:6][NH:5][C:4](=[O:19])[CH2:3][C@@H:2]([C:20]([OH:22])=[O:21])[NH2:1]

Komponenten

Versuchsvorschrift

The fully protected derivative Z-Asn(Tmob)-OBzl prepared in Step 1 (2.0 g, 3.75 mmol) was dissolved in acetic acid (50 ml), water (14 ml) and DMF (10 ml) by slight warming and vigorous stirring, nitrogen was flushed through the low pressure hydrogenation flask, 5% palladium on carbon catalyst (400 mg) was added, and a gentle stream of hydrogen continuously passed over the vigorously stirred solution for 2 hours. Nitrogen was once more flushed through the system and the catalyst removed by filtration through a doubled fluted Whatman No. 1 filter paper. The filtrate was evaporated, the residue dried in vacuo, and triturated under ethyl acetate to give a white solid. The suspension was cooled overnight to 4 degrees, then filtered and washed with ethyl acetate. Yield after drying 1.16 g (96%), Rf 0.55 single spot n-butanol/acetic acid/water (3:1:1).