Hydrochloric Acid → HDArg(Tos)-Leu-MetNH2

HRID 2418599Notes

Reaction equation

HRID 2418599 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:20]([NH:22][C@H:23]([C:28]([NH:30][C@H:31]([C:36]([NH2:38])=[O:37])[CH2:32][CH2:33][S:34][CH3:35])=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26])=[O:21])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:19])[NH:8][S:9]([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10].Cl>O1CCOCC1>[NH2:1][C@@H:2]([C:20]([NH:22][C@H:23]([C:28]([NH:30][C@H:31]([C:36]([NH2:38])=[O:37])[CH2:32][CH2:33][S:34][CH3:35])=[O:29])[CH2:24][CH:25]([CH3:26])[CH3:27])=[O:21])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:19])[NH:8][S:9]([C:12]1[CH:13]=[CH:14][C:15]([CH3:16])=[CH:17][CH:18]=1)(=[O:10])=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178503709HCID 178503709, compound

Product 1

HCID 178503710HDArg(Tos)-Leu-MetNH2Yield 45%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Condensation of BocDArg(Tos)OH (2.14 g.) and HLeu-MetNH2 hydrochloride salt (Example 1, 1.49 g.) using dicyclohexylcarbodiimide and 1-hydroxybenzotriazole gave BocDArg(Tos)-Leu-MetNH2 in 54% yield. De-t-butoxycarbonylation of BocDArg(Tos)-Leu-MetNH2 (1.7 g.) using hydrogen chloride in dioxane gave HDArg(Tos)-Leu-MetNH2 in 45% yield.

Sources & evidence

ORD record
ord-6bb1328615d7485db19e1730a8230b1a
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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