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Triethylamine → (E)-N1-(3-(1H-imidazol-1-yl)propyl)-2-((naphthalen-1-yloxy)methyl)-N8-(tetra hydro-2H-pyran-2-yloxy)-2-octenediamide

HRID 555359
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 555359
[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:32])/[C:11](/[CH2:20][O:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][C:17](O)=[O:18])[CH:5]=[CH:4][N:3]=[CH:2]1.C(N(CC)CC)C.Cl.C(N(CC)CCCN=C=NCC)C.[O:54]1[CH2:59][CH2:58][CH2:57][CH2:56][CH:55]1[O:60][NH2:61]>CN(C)C=O>[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:32])/[C:11](/[CH2:20][O:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([NH:61][O:60][CH:55]2[CH2:56][CH2:57][CH2:58][CH2:59][O:54]2)=[O:18])[CH:5]=[CH:4][N:3]=[CH:2]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 99645121-(3-Diethylaminopropyl)-3-ethylcarbodiimide hydrochlorideHCID 66987029(E)-8-(3-(1H-imidazol-1-yl)propylamino)-7-((naphthalen-1-yloxy)methyl)-8-oxo-6-octenoic acid

Produkt 1

HCID 86640100
(E)-N1-(3-(1H-imidazol-1-yl)propyl)-2-((naphthalen-1-yloxy)methyl)-N8-(tetra hydro-2H-pyran-2-yloxy)-2-octenediamide
Ausbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(E)-8-(3-(1H-imidazol-1-yl)propylamino)-7-((naphthalen-1-yloxy)-methyl)-8-oxo-6-octenoic acid (286 mg, 0.65 mM) obtained in Example (2-1-2) was dissolved in dimethylformamide (3 ml), and triethylamine (136 μl, 0.98 mM) was added thereto. Then, the resulting mixture was cooled to 0° C., and to the mixture, N-hydroxy-6-trifluorobenzotriazole (144 mg, 0.72 mM), 1-(3-diethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) (162 mg, 0.85 mM) and tetrahydropyranyloxyamine (114 mg, 0.98 mM) were added and stirred at room temperature for 18 hrs. After the completion of reaction, ice water was added to the reaction mixture. The resulting mixture was extracted with ethyl acetate. The organic layer was separated, washed with an aqueous saturated sodium bicarbonate solution and brine in order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography to obtain 220 mg of the title compound (yield 63%).

Aufarbeitung

  1. additionwas added to the reaction mixture
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with an aqueous saturated sodium bicarbonate solution and brine in order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue thus obtained

Quellen und Nachweise

ORD-Eintrag
ord-86bcd79d09e5474481139d8ff20fa5cc
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08053435B2

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