p-Methylphenethylamine → Nalpha-Benzyl-Ndelta-Boc-Nalpha-Methylornithine 2-(4-Methylphenyl)ethylamide

HRID 1067070Notes

Reaction equation

HRID 1067070 reaction equation
[CH2:1]([N:8]([CH3:24])[C@H:9]([C:21]([OH:23])=O)[CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][NH2:34])=[CH:28][CH:27]=1>>[CH3:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][NH:34][C:21](=[O:23])[C@H:9]([CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH3:24])=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 76751p-MethylphenethylamineHCID 57299805Nalpha-benzyl-Ndelta-Boc-Nalpha-methylornithine

Product 1

HCID 131722645Nalpha-Benzyl-Ndelta-Boc-Nalpha-Methylornithine 2-(4-Methylphenyl)ethylamide

Procedure

Nα-Benzyl-Nδ-Boc-Nα-methylornithine (200 mg) and 2-(4-methylphenyl)ethylamine were coupled to afford the titled compound (108 mg) as a glassy solid: 1H NMR (400 MHz, CDCl3) δ1.45 (s, 9H), 1.58 (m, 1H), 1.65 (m, 2H), 1.75 (m, 1H), 2.13 (s, 3H), 2.35 (s, 3H), 2.81 (t, J=5.8 Hz, 2H), 3.02 (m, 1H), 3.15 (m, 2H), 3.58 (m, 4H), 7.09 (m, 6H), and 7.27 (m, 3H).

Sources & evidence

ORD record
ord-d44d0aeb14c24e7089078442263b4e9e
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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