L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl- → Boc-Tyrosyl-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][C:38]1[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=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][C:38]1[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=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, crude Nδ-Boc-Nα-methylornithinyl 2-naphthyl ether (133 mg) and Boc-tyrosine (222 mg) is coupled to afford intermediate (125 mg) as a glassy solid: 1H NMR (400 MHz, CDCl3) δ1.44 (m, 21H), 1.63 (m, 1H), 2.75 (s, 3H), 3.15 (m, 2H), 3.92 (m, 2H), 4.84 (m, 1H), 5.06 (m, 1H), 6.62 (d, J=10.2 Hz, 2H), 7.08 (m, 4H), 7.35 (m, 1H), 7.42 (m, 1H), 7.66 (d, J=10.9 Hz, 1H), and 7.75 (m, 3H).
Sources & evidence
- ORD record
- ord-327b30743d914a00a68f605d0d7c77b9
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06245746B1
Reaction notes
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