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

HRID 1712903Notes

Reaction equation

HRID 1712903 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1049PyridineSolvent

Procedure

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 10 [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, 1993, 30 (October-November), 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 min. 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 11 (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.

Workup

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

Sources & evidence

ORD record
ord-2ebdb08de3a345578b4ecb23258387cc
Source dataset
uspto-grants-2010_09
Patent number
US07795238B2

Reaction notes

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