5'-O-(4,4'-Dimethoxytrityl)-2'-O-[2-(N-methylcarbamoyl)ethyl]-4-N-acetylcytidine → HCID 178485724, Verbindung

HRID 1665826

Reaktionsgleichung

Reaktionsgleichung von HRID 1665826
[CH3:1][O:2][C:3]1[CH:49]=[CH:48][C:6]([C:7]([O:22][CH2:23][C@H:24]2[O:28][C@@H:27]([N:29]3[CH:39]=[CH:38][C:33]([NH:34][C:35](=[O:37])[CH3:36])=[N:32][C:30]3=[O:31])[C@H:26]([O:40][CH2:41][CH2:42][C:43](=[O:46])[NH:44][CH3:45])[C@@H:25]2[OH:47])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.C(N(C(C)C)[P:54]([N:61]([CH:65]([CH3:67])[CH3:66])[CH:62]([CH3:64])[CH3:63])[O:55]OCCC#N)(C)C.[NH:71]1[C-:75]=NN=N1.[CH:76]([NH2+]C(C)C)(C)[CH3:77]>C(#N)C>[C:75]([CH2:76][CH2:77][PH:54]([O:47][C@@H:25]1[C@@H:24]([CH2:23][O:22][C:7]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[C:6]2[CH:48]=[CH:49][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[O:28][C@@H:27]([N:29]2[CH:39]=[CH:38][C:33]([NH:34][C:35](=[O:37])[CH3:36])=[N:32][C:30]2=[O:31])[C@@H:26]1[O:40][CH2:41][CH2:42][C:43](=[O:46])[NH:44][CH3:45])([N:61]([CH:62]([CH3:63])[CH3:64])[CH:65]([CH3:66])[CH3:67])[OH:55])#[N:71]

Komponenten

5

Edukt 3

HCID 532532925'-O-(4,4'-Dimethoxytrityl)-2'-O-[2-(N-methylcarbamoyl)ethyl]-4-N-acetylcytidineHCID 866383062-cyanoethoxy N,N,N',N'-tetraisopropylphosphorodiamiditeHCID 178458033HCID 178458033, Verbindung

Produkt 1

HCID 178485724HCID 178485724, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

The compound (480 mg, 0.71 mmol) prepared in Example 24 was dissolved in dried acetonitrile (2 mL). To the solution was added 2-cyanoethoxy N,N,N′,N′-tetraisopropylphosphorodiamidite (343 μL, 1.07 mmol) dissolved in dried acetonitrile (2 mL) and then diisopropylammonium 1H-tetrazolide (92 mg, 0.54 mmol), followed by vigorous stirring at room temperature for 15 hours. The reaction was terminated with a small amount of water, and then the reaction system was concentrated under reduced pressure, diluted with chloroform, and washed with saturated brine. The organic layer was dried with anhydrous sodium sulfate, and filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography eluting with chloroform:methanol:triethylamine (98:1.5:0.5) to give the title compound (300 mg, 0.34 mmol).

Aufarbeitung

  1. customThe reaction was terminated with a small amount of water
  2. concentrationthe reaction system was concentrated under reduced pressure
  3. additiondiluted with chloroform
  4. washwashed with saturated brine
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate, and filtrate
  6. concentrationwas concentrated under reduced pressure
  7. washeluting with chloroform:methanol:triethylamine (98:1.5:0.5)

Quellen und Nachweise

ORD-Eintrag
ord-daea591bed8c44648f844e41ec12ab51
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039611B2

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