Z-Asn-onp → HCID 178501420, compound
Reaction equation
[NH2:1][C@H:2]([C:15]([NH:17][C@H:18]([C:26]([NH:28][C@H:29]([C:36]([O:38][CH3:39])=[O:37])[CH2:30][C:31]1[N:35]=[CH:34][NH:33][CH:32]=1)=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[CH:40]1[CH:45]=[CH:44][C:43]([CH2:46][O:47][C:48]([NH:50][C@H:51]([C:56](OC2C=CC([N+]([O-])=O)=CC=2)=[O:57])[CH2:52][C:53]([NH2:55])=[O:54])=[O:49])=[CH:42][CH:41]=1>CN(C)C=O>[NH:50]([C:48]([O:47][CH2:46][C:43]1[CH:44]=[CH:45][CH:40]=[CH:41][CH:42]=1)=[O:49])[C@H:51]([C:56]([NH:1][C@H:2]([C:15]([NH:17][C@H:18]([C:26]([NH:28][C@H:29]([C:36]([O:38][CH3:39])=[O:37])[CH2:30][C:31]1[N:35]=[CH:34][NH:33][CH:32]=1)=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])=[O:57])[CH2:52][C:53](=[O:54])[NH2:55]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
5.4 g of H-Lys(BOC)-Phe-His-OMe (compare Example 1) and 4.5 g of Z-Asn-ONP in 20 ml of dimethylformamide are stirred for 20 hours at room temperature. The peptide derivative is precipitated by adding ethyl acetate, filtered off and washed with ether. After recrystallisation from methanol the product melts at 182°-183°C. In a thin layer chromatogram RF100 = 0.57 (on silica gel). [α]D20 = -28° (c = 1 in dimethylformamide).