Sulfuric Acid → 5'-[(2-Aminooxyethyl)methylamino]-5'-deoxy-8-methyladenosine sulfate

HRID 473571

Reaktionsgleichung

Reaktionsgleichung von HRID 473571
C(OC(=[N:6][O:7][CH2:8][CH2:9][N:10]([CH3:30])[CH2:11][C@H:12]1[O:16][C@@H:15]([N:17]2[C:26]3[N:25]=[CH:24][N:23]=[C:21]([NH2:22])[C:20]=3[N:19]=[C:18]2[CH3:27])[C@H:14]([OH:28])[C@@H:13]1[OH:29])C)C.C([O-])(O)=O.[Na+].[OH:36][S:37]([OH:40])(=[O:39])=[O:38]>>[S:37]([OH:40])([OH:39])(=[O:38])=[O:36].[NH2:6][O:7][CH2:8][CH2:9][N:10]([CH3:30])[CH2:11][C@H:12]1[O:16][C@@H:15]([N:17]2[C:26]3[N:25]=[CH:24][N:23]=[C:21]([NH2:22])[C:20]=3[N:19]=[C:18]2[CH3:27])[C@H:14]([OH:28])[C@@H:13]1[OH:29]

Komponenten

4

Edukt 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 866496695'-Deoxy-5'-[[2-[[(1-ethoxyethylidene)amino]oxy]ethyl]methylamino]-8-methyladenosine

Produkt 1

HCID 445641755'-[(2-Aminooxyethyl)methylamino]-5'-deoxy-8-methyladenosine sulfate

Versuchsvorschrift

Compound 6a (50 mg, 0.11 mmol) was dissolved in 2 mL of 2N H2SO4 and stirred for 2 days at room temperature. The reaction mixture was neutralized with NaHCO3 and lyophilized. The compound was extracted with EtOH (2×10 mL) and concentrated to dryness. The residue was purified by column chromatography (silica gel 230-400 mesh, elution with 7:1:0.3 chloroform:methanol:NH4OH). The desired fractions were combined, concentrated, and dried in vacuo. The product was dissolved in 3 mL of EtOH and 2N H2SO4 was added dropwise. The resulting sulfate salt that precipitated out was filtered, and washed with EtOH. This product, which was hygroscopic in nature, was dissolved in water (2 mL) and lyophilized to give a white solid: yield 20 mg (29%), MS: m/z 354 (M+H)+; 1HNMR (DMSO-d6) δ 8.25 (s, 1H, H-2), 7.80 (bs, 2H, O—NH2), 5.87 (d, 1H, H-1′, J1′,2′=5.7 Hz), 4.88 (t, 1H, H-2′, J2′,3′=5.2 Hz), 4.35-4.40 (bm, 1H, H-4′), 4.23 (t, 1H, H-3′, J2′,3′=3.2 Hz), 4.10 (t, 2H, NH2O—CH2), 3.50-3.57 (m, 1H, 5′-CH2), 3.65-3.72 (m, 1H, 5′-CH2), 3.45 (bm, 2H, N(CH3)—CH2), 2.85 (s, 3H, N—CH3), 2.58 (s, 3H, 8-CH3); UV λmax, nm, pH 1, 274 (∈ 15,200), pH 7, 276 (∈ 15,500), pH 13, 277 (∈ 15,900). Anal. (C14H23N7O4.2.2H2SO4.0.1C2H5OH.0.5H2O) C, H, N.

Aufarbeitung

  1. extractionThe compound was extracted with EtOH (2×10 mL)
  2. concentrationconcentrated to dryness
  3. customThe residue was purified by column chromatography (silica gel 230-400 mesh, elution with 7:1:0.3 chloroform:methanol:NH4OH)
  4. concentrationconcentrated
  5. customdried in vacuo
  6. dissolutionThe product was dissolved in 3 mL of EtOH
  7. addition2N H2SO4 was added dropwise
  8. customThe resulting sulfate salt that precipitated out
  9. filtrationwas filtered
  10. washwashed with EtOH
  11. dissolutionwas dissolved in water (2 mL)
  12. customto give a white solid

Quellen und Nachweise

ORD-Eintrag
ord-c6b6a03140984585a7164caf31645f98
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637485B2

Verknüpfte Notizen

Wird geladen…