Dicyclohexylcarbodiimide → BocPro-Phe-MePhe-Gly-Leu-MetNH2

HRID 2418532Notes

Reaction equation

[N:1]1([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:35][CH2:34][CH2:33][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([N:16]([CH3:32])[C@H:17]([C:25]([NH:27][CH2:28][C:29]([OH:31])=O)=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[NH2:43][C@H:44]([C:50]([NH:52][C@H:53]([C:58]([NH2:60])=[O:59])[CH2:54][CH2:55][S:56][CH3:57])=[O:51])[CH2:45][CH2:46][CH:47](C)C.Cl.[CH:62]1(N=C=NC2CCCCC2)CCCCC1.ON1C(=O)CCC1=O>>[N:1]1([C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])[CH2:35][CH2:34][CH2:33][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([N:16]([CH3:32])[C@H:17]([C:25]([NH:27][CH2:28][C:29]([NH:43][C@H:44]([C:50]([NH:52][C@H:53]([C:58]([NH2:60])=[O:59])[CH2:54][CH2:55][S:56][CH3:57])=[O:51])[CH2:45][CH:46]([CH3:47])[CH3:62])=[O:31])=[O:26])[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:15])[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:4]

Participants

Reactant 4

HCID 10868Dicyclohexylcarbodiimide

HCID 80170N-Hydroxysuccinimide

HCID 131713702BocPro-Phe-MePhe-GlyOH

HCID 131713703HLeu-MetNH2 hydrochloride

Product 1

HCID 131713701BocPro-Phe-MePhe-Gly-Leu-MetNH2Yield 100%

Procedure

Condensation of BocPro-Phe-MePhe-GlyOH (0.76 g.) and HLeu-MetNH2 hydrochloride salt (Example 1, 0.39 g.) using dicyclohexylcarbodiimide and N-hydroxysuccinimide gave BocPro-Phe-MePhe-Gly-Leu-MetNH2 in 100% yield. De-t-butoxycarbonylation of BocPro-Phe-MePhe-Gly-Leu-MetNH2 (1.07 g.) using hydrogen chloride in acetic acid gave HPro-Phe-MePhe-Gly-Leu-MetNH2, which was isolated as the amorphous white solid phosphate (1:1) salt dihydrate in 22% yield.

Sources & evidence

ORD record: ord-715fe5a9b14646dc8ec12ffb084b5fe9
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472305

Reaction notes

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