L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)- → Boc-O-Benzylseryl-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:46](O)=[O:47])[CH2:37][O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=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:46](=[O:47])[C@H:36]([CH2:37][O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=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 (37 mg) and Boc-O-benzylserine (62 mg) was coupled to afford product (62 mg) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ1.49 (broad s, 21H), 1.77 (m, 1H), 3.08 (s, 3H), 3.17 (s, 2H), 3.64 (m, 2H), 4.05 (dd, J=13.0; 3.8 Hz, 1H), 4.14 (dd, J=13.0; 7.3 Hz, 1H), 4.52 (m, 3H), 4.91 (m, 1H), 7.05 (m, 2H), 7.20 (m, 3H), 7.32 (m, 3H), 7.41 (m, 1H), and 7.69 (m, 3H); mass spectrum (ES+) m/e 636 (M+1).
Sources & evidence
- ORD record
- ord-89ce8c981e10418e9abfe6b84b448b3e
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06245746B1
Reaction notes
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