Dicyclohexylcarbodiimide → BocDPhe-Leu-NleNH2

HRID 2418592Notes

Reaction equation

[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:2]([C:10]([NH:12][C@H:13]([C:18](O)=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:28][C@H:29]([C:34]([NH2:36])=[O:35])[CH2:30][CH2:31][CH2:32][CH3:33].Cl.C1(N=C=NC2CCCCC2)CCCCC1.ON1C(=O)CCC1=O>>[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:2]([C:10]([NH:12][C@H:13]([C:18]([NH:28][C@H:29]([C:34]([NH2:36])=[O:35])[CH2:30][CH2:31][CH2:32][CH3:33])=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Reactant 4

HCID 10868Dicyclohexylcarbodiimide

HCID 80170N-Hydroxysuccinimide

HCID 7334994BocDPhe-LeuOH

HCID 18531007H-Nle-NH2.HCl

Product 1

HCID 131713779BocDPhe-Leu-NleNH2Yield 60%

Procedure

Condensation of BocDPheOH (2.65 g.) and HLeuOBz hydrobromide salt (3.02 g.) by the mixed anhydride method using diphenylphosphinyl chloride gave BocDPhe-LeuOBz in 54% yield. Debenzylation of BocDPhe-LeuOBz (2.25 g.) by hydrogenation with palladium catalyst gave BocDPhe-LeuOH in 87% yield. Condensation of BocDPhe-LeuOH (1.50 g.) and HNleNH2 hydrochloride salt (0.667 g.) using dicyclohexylcarbodiimide and N-hydroxysuccinimide gave BocDPhe-Leu-NleNH2 in 60% yield. De-t-butoxycarbonylation of BocDPhe-Leu-NleNH2 (1.00 g.) using hydrogen chloride in acetic acid gave HDPhe-Leu-NleNH2 hydrochloride salt in 79% yield.

Sources & evidence

ORD record: ord-902e156a7df04929ade383147aa5a6fe
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472305

Reaction notes

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