Piperidine → HDLys(Boc)-Leu-MetNH2

HRID 2418596Notes

Reaction equation

HRID 2418596 reaction equation
[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@@H:2]([C:15]([NH:17][C@H:18]([C:23]([NH:25][C@H:26]([C:31]([NH2:33])=[O:32])[CH2:27][CH2:28][S:29][CH3:30])=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21])=[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].N1CCCCC1>CN(C)C=O>[NH2:1][C@@H:2]([C:15]([NH:17][C@H:18]([C:23]([NH:25][C@H:26]([C:31]([NH2:33])=[O:32])[CH2:27][CH2:28][S:29][CH3:30])=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 131713783FmocDLys(Boc)-Leu-MetNH2

Product 1

HCID 131713784HDLys(Boc)-Leu-MetNH2Yield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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-55641fda530143e6a71b98c8d01a7dbd
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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