Triethylamine → HCID 67429382, Verbindung

HRID 1662302Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662302
[C@@H:1]1([N:9]2[CH:13]=[C:12](I)[CH:11]=[C:10]2[N+:15]([O-:17])=[O:16])[O:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1.C(N(CC)CC)C.[CH2:25]([NH:28][C:29](=[O:33])[CH:30]([Cl:32])[Cl:31])[C:26]#[CH:27]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[C@@H:1]1([N:9]2[CH:13]=[C:12]([C:27]#[C:26][CH2:25][NH:28][C:29](=[O:33])[CH:30]([Cl:32])[Cl:31])[CH:11]=[C:10]2[N+:15]([O-:17])=[O:16])[O:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 132331222,2-Dichloro-N-(prop-2-yn-1-yl)acetamideHCID 67428497HCID 67428497, Verbindung2×

Produkt 1

HCID 67429382HCID 67429382, VerbindungAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

1-(2-Deoxy-β-D-ribofuranosyl)-4-iodo-2-nitropyrrole (Compound 1) (354 mg, 1.0 mmol), Pd(PPh3)4 (58 mg, 0.05 mmol), CuI (30 mg, 0.16 mmol) and triethylamine (209 μl, 1.5 mmol) were dissolved in DMF (3.5 ml), followed by addition of a 1 M DMF solution of N-(2-propynyl)-dichloroacetamide (1.5 ml, 1.5 mmol). After stirring at room temperature for 12 hours, the reaction mixture was partitioned between ethyl acetate and water, and the organic layer was washed three times with water. After drying over anhydrous sodium sulfate, the organic layer was concentrated and purified on a silica gel column (CH2Cl2:MeOH, 20:1, v/v) and by HPLC (34%-35% CH3CN, 12 minutes) to give Compound 3 (317 mg, 81%).

Aufarbeitung

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. washthe organic layer was washed three times with water
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. concentrationthe organic layer was concentrated
  5. custompurified on a silica gel column (CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-a544384df7cd4a3d95c7624335447614
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030478B2

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