Dicyclohexylcarbodiimide → BocPro-DTrp-Phe-DTrp-MeLeu-MetNH2

HRID 2418604Notes

Reaction equation

HRID 2418604 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:53]([N:55]([CH3:72])[C@H:56]([C:61]([NH:63][C@H:64]([C:69]([NH2:71])=[O:70])[CH2:65][CH2:66][S:67][CH3:68])=[O:62])[CH2:57][CH:58]([CH3:60])[CH3:59])=[O:54])[CH2:43][C:44]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[NH:46][CH:45]=1.C1(N=C=NC2CCCCC2)CCCCC1.ON1C(=O)CCC1=O>>[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:53]([N:55]([CH3:72])[C@H:56]([C:61]([NH:63][C@H:64]([C:69]([NH2:71])=[O:70])[CH2:65][CH2:66][S:67][CH3:68])=[O:62])[CH2:57][CH:58]([CH3:60])[CH3:59])=[O:54])[CH2:43][C:44]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[NH:46][CH:45]=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

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 131713758BocPro-DTrp-PheOHHCID 131713791HDTrp-MeLeu-MetNH2

Product 1

HCID 131713793BocPro-DTrp-Phe-DTrp-MeLeu-MetNH2Yield 64%

Procedure

Condensation of BocPro-DTrp-PheOH (Example 33, 1.65 g.) and HDTrp-MeLeu-MetNH2 (1.34 g.) using dicyclohexylcarbodiimide and N-hydroxysuccinimide gave BocPro-DTrp-Phe-DTrp-MeLeu-MetNH2 in 64% yield. De-t-butoxycarbonylation of BocPro-DTrp-Phe-DTrp-MeLeu-MetNH2 (1.70 g.) using trifluoroacetic acid in dimethyl sulfide and ethanedithiol gave HPro-DTrp-Phe-DTrp-MeLeu-MetNH2, which was isolated as the amorphous white solid phosphate (1:1) salt tetrahydrate in 67% yield.

Sources & evidence

ORD record
ord-4cb83c85ba774546b0274a2a481c77c0
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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