Diisopropylethylamine → N6-[1-(4-iodo-2-nitrophenyl)ethyl]-2'-deoxyadenosine

HRID 871788

Reaktionsgleichung

Reaktionsgleichung von HRID 871788
[C@@H:1]1([N:9]2[C:18]3[N:17]=[CH:16][N:15]=[C:13](O)[C:12]=3[N:11]=[CH:10]2)[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.C(N(CC)C(C)C)(C)C.[I:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]([NH2:37])[CH3:36])=[C:31]([N+:38]([O-:40])=[O:39])[CH:30]=1>CN(C=O)C>[I:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]([NH:37][C:13]2[C:12]3[N:11]=[CH:10][N:9]([C:18]=3[N:17]=[CH:16][N:15]=2)[C@@H:1]2[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]2)[CH3:36])=[C:31]([N+:38]([O-:40])=[O:39])[CH:30]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 668309681-(4-Iodo-2-nitrophenyl)ethylamineHCID 178521064HCID 178521064, Verbindung

Produkt 1

HCID 86620496N6-[1-(4-iodo-2-nitrophenyl)ethyl]-2'-deoxyadenosine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a suspension of 2′-deoxyinosine (150 mg, 0.6 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphonate (BOP, 379 mg, 0.86 mmol) in anhydrous DMF (1.5 mL), N,N-diisopropylethylamine (186 μL, 1.1 mmol) was added followed by the addition of a solution of 1-(4-iodo-2-nitrophenyl)ethylamine (460 mg, 1.57 mmol) in anhydrous DMF (0.5 mL). The mixture was stirred under nitrogen atmosphere for 48 hours. DMF was removed in vacuo, and the crude product was purified by silica gel column chromatography to yield N6-[1-(4-iodo-2-nitrophenyl)ethyl]-2′-deoxyadenosine dA.20 (204 mg, 65%, 1:1 mixture of diastereomers) as a white foam.

Aufarbeitung

  1. additionwas added
  2. customDMF was removed in vacuo
  3. customthe crude product was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8f8fb0adb2eb4fe3a5152f637490f8dc
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969535B2

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