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

HRID 871787

Reaktionsgleichung

Reaktionsgleichung von HRID 871787
[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.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[N+:55]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=1[CH:64]([NH2:66])[CH3:65])([O-:57])=[O:56]>CN(C=O)C>[N+:55]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=1[CH:64]([NH:66][C:13]1[C:12]2[N:11]=[CH:10][N:9]([C:18]=2[N:17]=[CH:16][N:15]=1)[C@@H:1]1[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1)[CH3:65])([O-:57])=[O:56]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 107257231-(2-Nitrophenyl)ethanamineHCID 178521064HCID 178521064, Verbindung

Produkt 1

HCID 86620495N6-[1-(2-nitrophenyl)ethyl]-2'-deoxyadenosine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a suspension of 2′-deoxyinosine (100 mg, 0.4 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP, 210 mg, 0.48 mmol) in anhydrous DMF (1 mL), N,N-diisopropylethylamine (100 μL, 0.6 mmol) was added followed by the addition of a solution of 1-(2-nitrophenyl)ethylamine (250 mg, 1.51 mmol) in DMF (1 mL). The reaction was stirred at room temperature for 64 hours. Silica gel 60 (1 g, 60-200 mesh) was added, and the mixture was evaporated in vacuo to dryness. The residue was purified by silica gel column chromatography to yield N6-[1-(2-nitrophenyl)ethyl]-2′-deoxyadenosine dA.19 (67 mg, 42%, 1:1 mixture of diastereomers) as a white foam.

Aufarbeitung

  1. additionwas added
  2. additionSilica gel 60 (1 g, 60-200 mesh) was added
  3. customthe mixture was evaporated in vacuo to dryness
  4. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-75154a7c8dce49cfb6c8b2bd34f7c4ae
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969535B2

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