(2S)-2-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acid → Boc-Homophenylalanyl-Ndelta-Boc-Nalpha-Methylornithinyl 2-Naphthyl Ether
Reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:12](=[O:27])[C@H:13]([CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[NH:14][CH3:15].[C:28]([NH:35][C@H:36]([C:45](O)=[O:46])[CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:12](=[O:27])[C@H:13]([CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[N:14]([C:45](=[O:46])[C@H:36]([CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[NH:35][C:28]([O:30][C:31]([CH3:34])([CH3:32])[CH3:33])=[O:29])[CH3:15]Participants
3
Procedure
Using Procedure D, coupling of Nδ-Boc-Nα-methylornithinyl 2-naphthyl ether (E) and Boc-homophenylalanine afforded titled compound as a glassy solid: 1H NMR (400 MHz, CDCl3) δ1.44 (2s, 18H), 1.58-1.70 (m, 4H), 1.98 (m, 2H), 2.73 (m, 2H), 2.83 (s, 3H), 3.18 (m, 2H), 4.08 (m, 2H), 4.61 (m, 1H), 7.09 (m, 2H), 7.35 (m, 5H), 7.49 (t, J=9.1 Hz, 1H), 7.59 (t, J=9.0 Hz, 1H), and 7.81 (3H).
Sources & evidence
- ORD record
- ord-dcf026901df64fe2b19e9428d42550c2
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06245746B1
Reaction notes
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