3-Phenylpropylamine → Nalpha-benzyl-Ndelta-Boc-Nalpha-methylornithine 3-phenylpropylamide

HRID 1067081Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1067081
[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.[C:67]1([CH2:73][CH2:74][CH2:75][NH2:76])[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1>O1CCCC1.C(OCC)(=O)C>[C:67]1([CH2:73][CH2:74][CH2:75][NH:76][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]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH3:24])[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1

Komponenten

7

Edukt 4

HCID 162593-PhenylpropylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 57299805Nalpha-benzyl-Ndelta-Boc-Nalpha-methylornithine

Produkt 1

HCID 86757003Nalpha-benzyl-Ndelta-Boc-Nalpha-methylornithine 3-phenylpropylamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of Nα-benzyl-Nδ-Boc-Nα-methylornithine (300 mg), diisopropylethylamine (326 μl), and anhydrous tetrahydrofuran (4 ml) was treated with PyBop (585 mg) at 0° C. for 10 min., followed by the addition of a solution of 3-phenylpropylamine (147 μl) in anhydrous tetrahydrofuran (2 ml). The resulting solution was stirred at ambient temperature for 4 hrs. The reaction 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 chromatography over silica gel (hexane/ethyl acetate) to give Nα-benzyl-Nδ-Boc-Nα-methylornithine 3-phenylpropylamide (370 mg): 1H NMR (400 MHz, CDCl3) δ1.43 (s, 9H), 1.6-1.9 (m, 6H), 2.2 (s, 3H), 2.65 (t, J=6.2 Hz, 2H), 3.0-3.4 (m, 5H), 3.64 (s, 2H), 4.8 (s, 1H), and 7.1-7.5 (m, 10H).

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 chromatography over silica gel (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1870c31753dc4171a39f72cd3c3308e9
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06245746B1

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