HCID 11059478, compound → HCID 10966793, compound

HRID 2116737Notes

Reaction equation

HRID 2116737 reaction equation
C([O:9][C@@H:10]1[C@H:14]([CH2:15][O:16]C(=O)C2C=CC=CC=2)[O:13][C@H:12]([N:25]2[CH:32]=[C:31]([F:33])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[CH2:11]1)(=O)C1C=CC=CC=1>CO.O>[C@H:12]1([N:25]2[CH:32]=[C:31]([F:33])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[O:13][C@@H:14]([CH2:15][OH:16])[C@@H:10]([OH:9])[CH2:11]1

Participants

4

Reactant 1

HCID 11059478HCID 11059478, compound

Product 1

HCID 10966793HCID 10966793, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 1-(3,5-di-O-benzoyl-2-deoxy-β-L-xylofuranosyl)-5-fluorouracil (6b) (0.25 g, 0.55 mmol) in ammoniacal methanol (25 ml) is stirred overnight at room temperature. The solution is evaporated under reduced pressure and the residue is evaporated several times with methanol. The crude material obtained is dissolved in water and the resulting solution is washed several times with chloroform. The aqueous phase is evaporated and the residue is directly crystallized from methanol to give 115 mg (yield 85%) of pure 7b: m.p.=198-200° C.; UV [EtOH 95] λmax 267 nm (ε, 8500), λmin 233 nm (ε, 2100); 1H NMR (DMSO-d6) δ ppm=11.79 (s, 1H, 3-NH), 8.16 (d, 1H, H-6; J=7.4 Hz), 6.05 (dd, 1H, H-1′; J=1.8 and 6.5 Hz), 5.38 (d, 1H, OH-3′; J=3.3 Hz), 4.73 (t, 1H, OH-5′; J=5.4 Hz), 4.30-4.20 (m, 1H, H-3′), 3.85-3.60 (m, 3H, H-4′,5′ and 5″), 2.60-2.50 (m, 1H, H-2′ partially obscured by DMSO-d5), 1.90 (dd, 1H H-2″; J=1.8 and 14.7 Hz); mass spectra (matrix: glycerol-thioglycerol, 50:50, v/v): FAB>0 339 [M+glycerol+H]+, 247 [M+H]+, 131 [BH2]+ and 115 [s]+; FAB<0 245 [M−H]− and 129 [B]−.

Workup

  1. customThe solution is evaporated under reduced pressure
  2. customthe residue is evaporated several times with methanol
  3. customThe crude material obtained
  4. washthe resulting solution is washed several times with chloroform
  5. customThe aqueous phase is evaporated
  6. customthe residue is directly crystallized from methanol

Sources & evidence

ORD record
ord-841083b3e146424aaf56ffce0561bfc9
Source dataset
uspto-grants-2008_10
Patent number
US07439351B2

Reaction notes

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