N-t-Butoxycarbonyl Statine benzyl ester → HCID 178445976, Verbindung
Reaktionsgleichung
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([NH:26][C@H:27]([C:34]([NH:36]N)=[O:35])[CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)=[O:25])[CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(N[C@@H:46]([CH2:60][CH:61]([CH3:63])[CH3:62])[C@@H:47]([OH:59])[CH2:48][C:49]([O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:50])=O)(C)(C)C>>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([NH:26][C@H:27]([C:34]([NH:36][C@@H:46]([CH2:60][CH:61]([CH3:63])[CH3:62])[C@@H:47]([OH:59])[CH2:48][C:49]([O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:50])=[O:35])[CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)=[O:25])[CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Komponenten
3
Versuchsvorschrift
The procedure described in Example 1(c) was repeated, but using 300 mg (0.6 mmole) of N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-L-histidine hydrazide and 180 mg of benzyl 4(S)-t-butoxycarbonylamino-3(S)-hydroxy-6-methylheptanoate. The resulting syrup was purified by silica gel column chromatography eluted with mixtures of chloroform and methanol ranging from 20:1 to 5:1. The solvent was removed by distillation under reduced pressure from the active fractions, and diethyl ether was added to the residue, to solidify it. This solid was finely pulverized and separated by filtration, giving 97 mg of the title compound as a white powdery solid, melting at 102°-109° C., [α]24 -31.0° (C=0.5 methanol).