Hydrochloric Acid → HDPhe-Leu-NleNH2 hydrochloride

HRID 2418593Notes

Reaction equation

HRID 2418593 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:10]([NH:12][C@H:13]([C:18]([NH:20][C@H:21]([C:26]([NH2:28])=[O:27])[CH2:22][CH2:23][CH2:24][CH3:25])=[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.[ClH:36]>C(O)(=O)C>[NH2:1][C@@H:2]([C:10]([NH:12][C@H:13]([C:18]([NH:20][C@H:21]([C:26]([NH2:28])=[O:27])[CH2:22][CH2:23][CH2:24][CH3:25])=[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.[ClH:36]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131713779BocDPhe-Leu-NleNH2

Product 1

HCID 131713780HDPhe-Leu-NleNH2 hydrochlorideYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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-718319fd03dc4a28beaff8ed351276dc
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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