HCID 25182694, Verbindung → 5'-Deoxy-5'-methylamino-8-ethyladenosine

HRID 473567

Reaktionsgleichung

Reaktionsgleichung von HRID 473567
[CH3:1][NH:2][CH2:3][C@H:4]1[O:8][C@@H:7]([N:9]2[C:18]3[N:17]=[CH:16][N:15]=[C:13]([NH2:14])[C:12]=3[N:11]=[C:10]2[CH3:19])[C@H:6]([OH:20])[C@@H:5]1[OH:21].Cl[CH2:23][C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2CC)[C@H](O)[C@@H]1O>CN.C(O)C>[CH3:1][NH:2][CH2:3][C@H:4]1[O:8][C@@H:7]([N:9]2[C:18]3[N:17]=[CH:16][N:15]=[C:13]([NH2:14])[C:12]=3[N:11]=[C:10]2[CH2:19][CH3:23])[C@H:6]([OH:20])[C@@H:5]1[OH:21]

Komponenten

4

Edukt 2

HCID 25182694HCID 25182694, VerbindungHCID 252327175'-Deoxy-5'-methylamino-8-methyladenosine

Produkt 1

HCID 252320015'-Deoxy-5'-methylamino-8-ethyladenosine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22028356Methylamine ethanolLösungsmittel

Versuchsvorschrift

The procedure was the same as reported above for 4a using 3b (1.00 g, 3.18 mmol) and 33% methylamine/ethanol solution (30 mL). After column chromatography (elution with 5:1:0.3 chloroform:methanol:NH4OH), a yellow glassy solid was obtained: 498 mg (50%); MS m/z 309 (M+H)+; 1HNMR (DMSO-d6) δ 8.08 (bs, 1H, H-2), 7.13 (bs, 2H, 6-NH2), 5.70 (d, 1H, H-1′, J1′,2′=6.6 Hz), 5.30 (d, 1H, 2′-OH, J2′-2′OH=6.4 Hz), 5.16 (d, 1H, 3′-OH, J3′-3′OH=4.5 Hz), 5.08 (ddd, 1H, H-2′, J1′,2′=6.6 Hz, J2′,3′=5.4 Hz, J2′-2′OH=6.4 Hz), 4.14-4.18 (m, 1H, H-3′), 3.96-4.0 (m, 1H, H-4′), 2.88 (q, 2H, 8-CH2CH3), 2.64-2.78 (m, 2H, 5′-CH2), 2.29 (s, 3H, 5′NH—CH3), 1.30 (t, 3H, 8CH2CH3).

Aufarbeitung

  1. washAfter column chromatography (elution with 5:1:0.3 chloroform:methanol:NH4OH)
  2. customa yellow glassy solid was obtained

Quellen und Nachweise

ORD-Eintrag
ord-a4d5d2622a6e4aa28c7ff1f90fb76c90
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637485B2

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