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

HRID 2418619Notes

Reaction equation

[N:1]1([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:31][CH2:30][CH2:29][C@H:2]1[C:3]([N:5]([CH3:28])[C@H:6]([C:14]([NH:16][C@H:17]([C:25](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].[NH2:39][CH2:40][C:41]([NH:43][C@H:44]([C:49]([NH:51][C@H:52]([C:57]([NH2:59])=[O:58])[CH2:53][CH2:54][S:55][CH3:56])=[O:50])[CH2:45][CH:46]([CH3:48])[CH3:47])=[O:42].C1(N=C=NC2CCCCC2)CCCCC1.ON1C(=O)CCC1=O>>[N:1]1([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:31][CH2:30][CH2:29][C@H:2]1[C:3]([N:5]([CH3:28])[C@H:6]([C:14]([NH:16][C@H:17]([C:25]([NH:39][CH2:40][C:41]([NH:43][C@H:44]([C:49]([NH:51][C@H:52]([C:57]([NH2:59])=[O:58])[CH2:53][CH2:54][S:55][CH3:56])=[O:50])[CH2:45][CH:46]([CH3:48])[CH3:47])=[O:42])=[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 7021411Gly-L-Leu-L-Met-NH2

HCID 131713811BocPro-MePhe-PheOH

Product 1

HCID 131713810BocPro-MePhe-Phe-Gly-Leu-MetNH2Yield 50%

Procedure

Condensation of BocPro-MePhe-PheOH (670 mg.) and HGly-Leu-MetNH2 (Example 7, 418 mg.) using dicyclohexylcarbodiimide and N-hydroxysuccinimide gave BocPro-MePhe-Phe-Gly-Leu-MetNH2 in 50% yield. De-t-butoxycarbonylation of BocPro-MePhe-Phe-Gly-Leu-MetNH2 (480 mg.) using hydrogen chloride in ethyl acetate gave HPro-MePhe-Phe-Bly-Leu-MetNH2, which was isolated as the amorphous white solid hydrochloride salt monohydrate in 85% yield.

Sources & evidence

ORD record: ord-e69bf57506594416b9ba772bfaa540f8
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472305

Reaction notes

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