Dicyclohexylcarbodiimide → HCID 178503709, compound

HRID 2418598Notes

Reaction equation

HRID 2418598 reaction equation
[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@@H:2]([C:20]([OH:22])=O)[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].[NH2:30][C@H:31]([C:37]([NH:39][C@H:40]([C:45]([NH2:47])=[O:46])[CH2:41][CH2:42][S:43][CH3:44])=[O:38])[CH2:32][CH2:33][CH:34](C)C.Cl.[CH:49]1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1>>[NH:1]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[C@@H:2]([C:20]([NH:30][C@H:31]([C:37]([NH:39][C@H:40]([C:45]([NH2:47])=[O:46])[CH2:41][CH2:42][S:43][CH3:44])=[O:38])[CH2:32][CH:33]([CH3:34])[CH3:49])=[O:22])[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

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 131713703HLeu-MetNH2 hydrochlorideHCID 178427598HCID 178427598, compound

Product 1

HCID 178503709HCID 178503709, compoundYield 54%

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-5218ec8967044e99b0715a5975325eee
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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