2-(4-Fluorophenyl)ethylamide → Ndelta-Boc-Nalpha-Benzyl-Nalpha-Methylornithine 2-(4-Fluorophenyl)ethylamide

HRID 1067066Notes

Reaction equation

HRID 1067066 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][CH2:11][C@@H:12]([C:22]([OH:24])=O)[N:13]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[F:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][NH-:34])=[CH:28][CH:27]=1>>[F:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][NH:34][C:22](=[O:24])[C@H:12]([CH2:11][CH2:10][CH2:9][NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[N:13]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH3:14])=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 536277222-(4-Fluorophenyl)ethylamideHCID 57299805Nalpha-benzyl-Ndelta-Boc-Nalpha-methylornithine

Product 1

HCID 131722641Ndelta-Boc-Nalpha-Benzyl-Nalpha-Methylornithine 2-(4-Fluorophenyl)ethylamide

Procedure

Nδ-Boc-Nα-benzyl-Nα-methylornithine and 2-(4-fluorophenyl)ethylamide were coupled, as per Procedure C, to afford titled compound as a glassy solid: 1H NMR (400 MHz, CDCl3) δ1.52 (s, 9H), 1.73 (m, 1H), 1.65 (m, 2H), 1.79 (m, 1H), 2.78 (t, J=7.9 Hz, 2H), 3.02 (m, 1H), 3.14 (m, 2H), 3.52 (m, 4H), 6.96 (m, 2H), 7.11 (m, 5H), and 7.28 (m, 2H).

Sources & evidence

ORD record
ord-6099a638d3984a9fbf11837a1b5b77ef
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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