Boc-3-(2-naphthyl)-L-alanine → Boc-beta-(2-Naphthyl)alanyl-Ndelta-Boc-Nalpha-Methylornithine 2-(4-Hydroxyphenyl)ethylamide

HRID 1067077Notes

Reaction equation

HRID 1067077 reaction equation
[C:1]([NH:8][C@H:9]([C:21](O)=[O:22])[CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][NH:33][C:34](=[O:49])[C@H:35]([CH2:38][CH2:39][CH2:40][NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[NH:36][CH3:37])=[CH:27][CH:26]=1>CO.C(Cl)Cl>[OH:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][NH:33][C:34](=[O:49])[C@H:35]([CH2:38][CH2:39][CH2:40][NH:41][C:42]([O:44][C:45]([CH3:46])([CH3:48])[CH3:47])=[O:43])[N:36]([C:21](=[O:22])[C@H:9]([CH2:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2])[CH3:37])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 7020908Boc-3-(2-naphthyl)-L-alanineHCID 131722652Ndelta-Boc-Nalpha-Methylornithine 2-(4-Hydroxyphenyl)ethylamide

Product 1

HCID 131722653Boc-beta-(2-Naphthyl)alanyl-Ndelta-Boc-Nalpha-Methylornithine 2-(4-Hydroxyphenyl)ethylamide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Using Procedure B, coupling of Boc-β-(2-naphthyl)alanine and Nδ-Boc-Nα-methylornithine 2-(4-hydroxyphenyl)ethylamide, followed by silica gel chromatography (2.5% MeOH/CH2Cl2): 1H NMR (400 MHz, CDCl3) 6 1.41 (m, 21H), 1.85 (m, 1H), 2.20 (m, 2H), 2.45 (m, 1H), 2.67 (m, 4H), 3.03 (m, 4H), 4.91 (m, 2H), 6.77 (m, 2H), 6.87 (d, J=8.7 Hz, 1H), 6.98 (d, J=10.0 Hz, 1H), 7.34 (m, 1H), 7.46 (m, 2H), 7.66 (m, 1H), and 7.78 (m, 3H); mass spectrum (ES+) m/e 663 (M+1).

Sources & evidence

ORD record
ord-36e68840ee9949a4b392726fa994b60e
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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