Dicyclohexylcarbodiimide → HCID 178503708, compound

HRID 2418600Notes

Reaction equation

HRID 2418600 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:60]([NH:62][C@H:63]([C:68]([NH:70][C@H:71]([C:76]([NH2:78])=[O:77])[CH2:72][CH2:73][S:74][CH3:75])=[O:69])[CH2:64][CH:65]([CH3:67])[CH3:66])=[O:61])[CH2:43][CH2:44][CH2:45][NH:46][C:47](=[NH:59])[NH:48][S:49]([C:52]1[CH:58]=[CH:57][C:55]([CH3:56])=[CH:54][CH:53]=1)(=[O:51])=[O:50].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:60]([NH:62][C@H:63]([C:68]([NH:70][C@H:71]([C:76]([NH2:78])=[O:77])[CH2:72][CH2:73][S:74][CH3:75])=[O:69])[CH2:64][CH:65]([CH3:66])[CH3:67])=[O:61])[CH2:43][CH2:44][CH2:45][NH:46][C:47](=[NH:59])[NH:48][S:49]([C:52]1[CH:53]=[CH:54][C:55]([CH3:56])=[CH:57][CH:58]=1)(=[O:50])=[O:51])=[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

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 131713758BocPro-DTrp-PheOHHCID 178503710HDArg(Tos)-Leu-MetNH2

Product 1

HCID 178503708HCID 178503708, compoundYield 46%

Procedure

Condensation of BocPro-DTrp-PheOH (Example 33, 658 mg.) and HDArg(Tos)-Leu-MetNH2 (630 mg.) using dicyclohexylcarbodiimide and 1-hydroxybenzotriazole gave BocPro-DTrp-Phe-DArg(Tos)-Leu-MetNH2 in 46% yield. De-t-butoxycarbonylation of BocPro-DTrp-Phe-DArg(Tos)-Leu-MetNH2 (524 mg.) using trifluoroacetic acid in dimethyl sulfide and ethanedithiol gave HPro-DTrp-Phe-DArg(Tos)-Leu-MetNH2 in 78% yield. De-p-toluenesulfonylation of HPro-DTrp-Phe-DArg(Tos)-Leu-MetNH2 (420 mg.) using liquid hydrogen fluoride with anisole gave HPro-DTrp-Phe-DArg-Leu-MetNH2, which was isolated as the amorphous off-white solid dihydrochloride acetate (2:1) salt hydrate (2:5) in 61% yield.

Sources & evidence

ORD record
ord-6f0d07d9ebb740c4a781c01fa63c3696
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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