L-Lysine → L-Lysinamide

HRID 1586248Notes

Reaction equation

HRID 1586248 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=O)[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].O.O[N:13]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1>CN(C)C=O>[NH2:1][C@H:2]([C:8]([NH2:13])=[O:10])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]

Participants

6

Reactant 4

HCID 5962L-LysineHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 439605L-LysinamideYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

L-Lysine, N-ε-(carbobenzoxy)-[N-ε-[N-[4-[4-(2-methyl-1H-imidazol-1-yl)-butyl]phenyl]acetyl]-L-(O-benzyl)-seryl]-, (150.0 mg, 0.21 mmol), 1-hydroxy-benzotriazole hydrate (31.1 mg, 0.21 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (40.1 mg, 0.21 mmol) were mixed in dimethylformamide (2.0 mL) at 0° C. for 15 minutes. N-Methylmorpholine (60.0 mg, 0.60 mmol) and methyl (R,S)-3-amino-3-cyclohexylpropionate (46 mg, 0.21 mmol) were added, and the solution was stirred at room temperature for 16 hours. The solvent was removed at reduced pressure, and the residue taken up in methanol (1.00 mL). The product was isolated as a waxy solid by preparative HPLC to give 136 mg (73%) of L-lysinamide, N-[1-cyclohexyl-2-carbomethoxyethyl]-N-ε-(carbobenzoxy)-[N-ε-[N-[4-[4-(2-methyl-1H-imidazol-1-yl)-butyl]phenyl]-acetyl]-L-(O-benzyl)-seryl]-, ±. HRMS calcd for C50H67N6O8 (M+H) 879.5020, found 879.5030.

Workup

  1. customThe solvent was removed at reduced pressure
  2. customThe product was isolated as a waxy solid by preparative HPLC

Sources & evidence

ORD record
ord-47e988b0501a4b94940330dd81fb7661
Source dataset
uspto-grants-1999_08
Patent number
US05942600

Reaction notes

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