2-Naphthylamine → Nalpha-benzyl-Ndelta-Boc-Nalpha-methylornithine 2-naphthyl-amide

HRID 1067083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1067083
[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]

Komponenten

7

Edukt 4

HCID 70572-NaphthylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 57299805Nalpha-benzyl-Ndelta-Boc-Nalpha-methylornithine

Produkt 1

HCID 86757006Nalpha-benzyl-Ndelta-Boc-Nalpha-methylornithine 2-naphthyl-amideAusbeute 68,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. washwashed with water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe product was purified by silica gel chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-ffcc695df24e44fe98a8f93003153425
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06245746B1

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