Dicyclohexylcarbodiimide → BocPro-DTrp-Phe-DLys(Boc)-Leu-MetNH2
Reaction equation
[N:1]1([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:33][CH2:32][CH2:31][C@H:2]1[C:3]([NH:5][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].[NH2:41][C@@H:42]([C:55]([NH:57][C@H:58]([C:63]([NH:65][C@H:66]([C:71]([NH2:73])=[O:72])[CH2:67][CH2:68][S:69][CH3:70])=[O:64])[CH2:59][CH:60]([CH3:62])[CH3:61])=[O:56])[CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1>>[N:1]1([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:33][CH2:32][CH2:31][C@H:2]1[C:3]([NH:5][C@@H:6]([C:17]([NH:19][C@H:20]([C:28]([NH:41][C@@H:42]([C:55]([NH:57][C@H:58]([C:63]([NH:65][C@H:66]([C:71]([NH2:73])=[O:72])[CH2:67][CH2:68][S:69][CH3:70])=[O:64])[CH2:59][CH:60]([CH3:62])[CH3:61])=[O:56])[CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:48]([O:50][C:51]([CH3:53])([CH3:54])[CH3:52])=[O:49])=[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-DTrp-PheOH (0.88 g.) and HDLys(Boc)-Leu-MetNH2 (0.68 g.) using dicyclohexylcarbodiimide and 1-hydroxybenzotriazole gave BocPro-DTrp-Phe-DLys(Boc)-Leu-MetNH2 in 46% yield. De-t-butoxycarbonylation of BocPro-DTrp-Phe-DLys(Boc)-Leu-MetNH2 (560 mg.) using trifluoroacetic acid in dimethyl sulfide and ethanedithiol gave HPro-DTrp-Phe-DLys-Leu-MetNH2, which was isolated as the amorphous white solid phosphate (1:1) acetate (1:3) salt in 26% yield.
Sources & evidence
- ORD record
- ord-00884829127a410198d9834ab176b237
- Source dataset
- uspto-grants-1984_09
- Patent number
- US04472305
Reaction notes
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