Acetone → 1-(3,5-Di-O-benzoyi-beta-L-xylofuranosyl)uracil

HRID 456388Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456388
O.NN.C([O:7][C@H:8]1[C@H:12]([O:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:11]([CH2:22][O:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:10][C@@H:9]1[N:32]1[CH:39]=[CH:38][C:36](=[O:37])[NH:35][C:33]1=[O:34])(=O)C.CC(C)=O>N1C=CC=CC=1.C(O)(=O)C>[C:14]([O:13][C@@H:12]1[C@H:11]([CH2:22][O:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:10][C@H:9]([N:32]2[CH:39]=[CH:38][C:36](=[O:37])[NH:35][C:33]2=[O:34])[C@H:8]1[OH:7])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 3

HCID 180AcetoneHCID 24654Hydrazine hydrate (1:1)HCID 103456211-(2-O-acetyl-3,5-di O-benzoyl-beta-L-xylofuranosyl)uracil

Produkt 1

HCID 667170671-(3,5-Di-O-benzoyi-beta-L-xylofuranosyl)uracilAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

Hydrazine hydrate (1.4 mL, 28.7 mmol) was added to a solution of 1-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)uracil 1 [Ref.: Gosselin, G.; Bergogne, M.-C.; Imbach, J.-L., “Synthesis and Antiviral Evaluation of β-L-Xylofuranosyl Nucleosides of the Five Naturally Occurring Nucleic Acid Bases”, Journal of Heterocyclic Chemistry, October–November 1993, 30, 1229–1233] (4.79 g, 9.68 mmol) in pyridine (60 mL) and acetic acid (15 mL). The solution was stirred overnight at room temperature. Acetone was added (35 mL) and the mixture was stirred for 30 minutes. The reaction mixture was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography [eluent: stepwise gradient of methanol (0–4%) in dichloromethane to give 2 (3.0 g, 68%) which was crystallized from cyclohexane/dichloromethane: mp=111–114° C.; 1H-NMR (DMSO-d6): δ 11.35 (br s, 1H, NH), 7.9–7.4 (m, 11H, 2 C6H5CO, H-6), 6.38 (d, 1H, OH-2′, JOH-2′=4.2 Hz), 5.77 (d, 1H, H-1′, J1′-2′=1.9 Hz), 5.55 (d, 1H, H-5, J5-6=8 Hz), 5.54 (dd, 1H, H-3′, J3′-2′=3.9 Hz and J3′-4′=1.8 Hz), 4.8 (m, 1H, H-4′), 4.7 (m, 2H, H-5′ and H-5″), 4.3 (m, 1H, H-2′); MS: FAB>0 (matrix GT) m/z 453 (M+H)+, 105 (C6H5CO)+; FAB<0 (matrix GT) m/z 451 (M−H)−, 121 (C6H5CO2)−, 111 (B)−; Anal. Calcd for C23H20N2O8.H2O: C, 58.09; H, 4.76; N, 5.96. Found: C, 57.71; H, 4.42; N, 5.70.

Aufarbeitung

  1. stirringthe mixture was stirred for 30 minutes
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography [eluent

Quellen und Nachweise

ORD-Eintrag
ord-29727ba985204fcf84056f99ed090cd4
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186700B2

Notizen zur Reaktion

Wird geladen…