Dicyclohexylcarbodiimide → FmocDLys(Boc)-Leu-MetNH2

HRID 2418595Notes

Reaction equation

HRID 2418595 reaction equation
[NH:1]([C:18]([O:20][CH2:21][CH:22]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[C@@H:2]([C:15](O)=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[NH2:35][C@H:36]([C:42]([NH:44][C@H:45]([C:50]([NH2:52])=[O:51])[CH2:46][CH2:47][S:48][CH3:49])=[O:43])[CH2:37][CH2:38][CH:39](C)C.Cl.[CH:54]1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1>>[NH:1]([C:18]([O:20][CH2:21][CH:22]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[C@@H:2]([C:15]([NH:35][C@H:36]([C:42]([NH:44][C@H:45]([C:50]([NH2:52])=[O:51])[CH2:46][CH2:47][S:48][CH3:49])=[O:43])[CH2:37][CH:38]([CH3:39])[CH3:54])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 13585941(2R)-6-(((tert-butoxy)carbonyl)amino)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acidHCID 131713703HLeu-MetNH2 hydrochloride

Product 1

HCID 131713783FmocDLys(Boc)-Leu-MetNH2Yield 87%

Procedure

Condensation of FmocDLys(Boc)OH (1.00 g.) and HLeu-MetNH2 hydrochloride salt (Example 1, 0.63 g.) using dicyclohexylcarbodiimide and 1-hydroxybenzotriazole gave FmocDLys(Boc)-Leu-MetNH2 in 87% yield. De-9-fluorenylmethoxycarbonylation of FmocDLys(Boc)-Leu-MetNH2 (1.00 g.) using piperidine in dimethylformamide gave HDLys(Boc)-Leu-MetNH2 in 100% yield.

Sources & evidence

ORD record
ord-2655aed522b449ecaffa0aab6ded66d9
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

Loading…