L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl- → Boc-Tyrosyl-Ndelta-Boc-Nalpha-Methylornithine beta-Naphthylamide
Reaction equation
[C:1]([NH:8][C@H:9]([C:18]([OH:20])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1[NH:31][C:32](=[O:47])[C@H:33]([CH2:36][CH2:37][CH2:38][NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[NH:34][CH3:35]>>[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1[NH:31][C:32](=[O:47])[C@H:33]([CH2:36][CH2:37][CH2:38][NH:39][C:40]([O:42][C:43]([CH3:45])([CH3:44])[CH3:46])=[O:41])[N:34]([C:18](=[O:20])[C@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH3:35]Participants
3
Procedure
Boc-tyrosine (400 mg) and Nδ-Boc-Nα-methylornithine β-naphthylamide (454 mg) were coupled (Procedure B) to afford titled compound (447 mg) as a glassy solid: 1H NMR (400 MHz, CDCl3) δ1.50 (m, 21H), 1.77 (m, 1H), 2.73 (s, 3H), 2.76 (m, 2H), 2.99 (dd, J=10.8; 6.8 Hz, 1H), 3.09 (dd, J=12.8; 13.2 Hz, 1H), 4.70 (m, 1H), 4.87 (m, 1H), 6.89 (d, J=8.0 Hz, 2H), 7.09 (d, J=8.0 Hz, 2H), 7.41 (m, 2H), 7.75 (m, 4H), and 8.26 (s, 1H).
Sources & evidence
- ORD record
- ord-d464d0e5010e41d89be1aa39e4b906d4
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06245746B1
Reaction notes
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