2-Naphthylamine → Nalpha-benzyl-Ndelta-Boc-Nalpha-methylornithine 2-naphthyl-amide
Reaction equation
[CH2:1]([N:8]([CH3:24])[C@H:9]([C:21]([OH:23])=O)[CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:67][C:68]1[CH:77]=[CH:76][C:75]2[C:70](=[CH:71][CH:72]=[CH:73][CH:74]=2)[CH:69]=1>C(OCC)(=O)C.O1CCCC1>[CH:69]1[C:70]2[C:75](=[CH:74][CH:73]=[CH:72][CH:71]=2)[CH:76]=[CH:77][C:68]=1[NH:67][C:21](=[O:23])[C@H:9]([CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:24]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of Nα-benzyl-Nδ-Boc-Nα-methylornithine (2.13 g, 6.3 mmol), diisopropyl-ethylamine (2.2 ml, 12.6 mmol), and anhydrous tetrahydrofuran (20 ml) was treated with PyBop (4 g, 7.6 mmol) at 0° C. for 10 min., followed by the addition of β-amino-naphthalene (1.09 g, 7.6 mmol). The resulting solution was stirred at ambient temperature overnight, and the reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The product was purified by silica gel chromatography (hexane/ethyl acetate) to afford Nα-benzyl-Nδ-Boc-Nα-methylornithine 2-naphthyl-amide (2 g): 1H NMR (400 MHz, CDCl3) δ1.43 (s, 9H), 1.6-1.9 (m, 4H), 2.38 (s, 3H), 3.2-3.3 (m, 2H), 3.7-3.8 (m, 2H), 4.7 (s, 1H), 7.25-7.8 (m, 11H), and 8.25 (s, 1H).
Workup
- washwashed with water
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customThe product was purified by silica gel chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-ffcc695df24e44fe98a8f93003153425
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06245746B1
Reaction notes
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