Dicyclohexylcarbodiimide → BocPro-MeDTrp-Phe-DTrp-Leu-MetNH2
Reaction equation
[N:1]1([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:34][CH2:33][CH2:32][C@H:2]1[C:3]([N:5]([CH3:31])[C@@H:6]([C:17]([NH:19][C@H:20]([C:28](O)=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:18])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:4].[NH2:42][C@@H:43]([C:54]([NH:56][C@H:57]([C:62]([NH:64][C@H:65]([C:70]([NH2:72])=[O:71])[CH2:66][CH2:67][S:68][CH3:69])=[O:63])[CH2:58][CH:59]([CH3:61])[CH3:60])=[O:55])[CH2:44][C:45]1[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[NH:47][CH:46]=1.CC(O)=O.C1(N=C=NC2CCCCC2)CCCCC1.ON1C(=O)CCC1=O>>[N:1]1([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:34][CH2:33][CH2:32][C@H:2]1[C:3]([N:5]([CH3:31])[C@@H:6]([C:17]([NH:19][C@H:20]([C:28]([NH:42][C@@H:43]([C:54]([NH:56][C@H:57]([C:62]([NH:64][C@H:65]([C:70]([NH2:72])=[O:71])[CH2:66][CH2:67][S:68][CH3:69])=[O:63])[CH2:58][CH:59]([CH3:61])[CH3:60])=[O:55])[CH2:44][C:45]1[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[NH:47][CH:46]=1)=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:18])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:4]Participants
5
Procedure
Condensation of BocPro-MeDTrp-PheOH (3.68 g.) and HDTrp-Leu-MetNH2 acetate salt (part B of Example 17, 3.32 g.) using dicyclohexylcarbodiimide and N-hydroxysuccinimide gave BocPro-MeDTrp-Phe-DTrp-Leu-MetNH2 in 20% yield. De-t-butoxycarbonylation of BocPro-MeDTrp-Phe-DTrp-Leu-MetNH2 (1.00 g.) using trifluoroacetic acid in methyl ethyl sulfide and ethanedithiol gave HPro-MeDTrp-Phe-DTrp-Leu-MetNH2, which was isolated as the amorphous white solid phosphate salt monohydrate in 67% yield.
Sources & evidence
- ORD record
- ord-020aaa0fecd04f758bd0ccc3a8a59a09
- Source dataset
- uspto-grants-1984_09
- Patent number
- US04472305
Reaction notes
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