(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1,3-thiazol-2-yl)propanoic acid → Boc-beta-(2-Thiazolyl)alanyl-Ndelta-Boc-Nalpha-Methylornithine beta-Naphthylamide
Reaction equation
[C:1]([NH:8][C@H:9]([C:16]([OH:18])=O)[CH2:10][C:11]1[S:12][CH:13]=[CH:14][N:15]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[NH:29][C:30](=[O:45])[C@H:31]([CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[NH:32][CH3:33]>>[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[NH:29][C:30](=[O:45])[C@H:31]([CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][C:41]([CH3:43])([CH3:42])[CH3:44])=[O:39])[N:32]([C:16](=[O:18])[C@H:9]([CH2:10][C:11]1[S:12][CH:13]=[CH:14][N:15]=1)[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH3:33]Participants
3
Procedure
Boc-β-(2-thiazolyl)alanine and Nδ-Boc-Nα-methylornithine β-naphthylamide were coupled under the conditions described in Procedure B, afforded a glassy solid which was purified by silica gel chromatography (1 to 2% MeOH/CH2Cl2): 1H NMR (400 MHz, CDCl3) δ1.45 (s, 9H), 1.50 (s, 9H), 1.52 (m, 2H), 1.77 (m, 1H), 2.18 (m, 1H), 3.01 (s, 3H), 3.19 (m, 3H), 3.49 (m, 1H), 4.98 (m,1H), 5.36 (m, 1H), 7.12 (s, 1H), 7.43 (m, 2H), 7.59 (d, J=7.2 Hz, 1H), 7.78 (m, 3H), 8.28 (s, 1H), 8.58 (s, 1H); mass spectrum (ES+) m/e 626 (M+1).
Workup
- customafforded a glassy solid which
- customwas purified by silica gel chromatography (1 to 2% MeOH/CH2Cl2)
Sources & evidence
- ORD record
- ord-dc210f8d347a47dcaec6543d51bb69d6
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06245746B1
Reaction notes
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