Methanol → HCID 86588187, compound

HRID 1839269Notes

Reaction equation

HRID 1839269 reaction equation
C(O[C@H:5]1[C@@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@H:8]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([Cl:32])=[N:18][C:19]=3[NH:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[F:31])[O:7][C@@H:6]1[CH2:33][O:34]C(=O)C)(=O)C.[CH3:38]O>C[O-].[Na+]>[Cl:32][C:17]1[N:16]=[C:15]2[C:20]([N:21]=[CH:22][N:14]2[C@H:8]2[C@@H:9]3[O:10][C:11]([CH3:12])([CH3:38])[O:13][C@@H:5]3[C@@H:6]([CH2:33][OH:34])[O:7]2)=[C:19]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[F:31])[N:18]=1

Participants

4

Reactant 2

HCID 887Methanol2×HCID 18336822HCID 18336822, compound

Product 1

HCID 86588187HCID 86588187, compound

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-[2-chloro-6-(4-chloro-2-fluoroanilino)-9H-purin-9-yl]tetrahydrofuran-3-yl acetate (400 mg) in methanol (7 ml), sodium methoxide, 25% in methanol, (3 drops) was added. On stirring for 15 min at 20° C. the reaction mixture went clear. On stirring at 20° C. for a further 90 min a precipitate formed. The precipitate was collected by filtration and dried in vacuo for 16 hours. This was dissolved in a mixture of acetone (15 ml) and 2-2-dimethoxypropane (3 ml), and para-toluene sulphonic acid (193 mg) added. The mixture was stirred at 20° C. for 3 hours. The solvent was removed in vacuo and the residue dissolved in ethyl acetate (50 ml), washed with water (50 ml) and brine (30 ml), dried (MgSO4) and the solvent removed in vacuo. Purification by chromatography on silica gel (Varian Bondelut cartridge), eluting with cyclohexane:ethyl acetate (1:1) gave the title compound as a white foam (240 mg).

Workup

  1. additionwas added
  2. stirringOn stirring at 20° C. for a further 90 min a precipitate
  3. customformed
  4. filtrationThe precipitate was collected by filtration
  5. customdried in vacuo for 16 hours
  6. dissolutionThis was dissolved in a mixture of acetone (15 ml) and 2-2-dimethoxypropane (3 ml), and para-toluene sulphonic acid (193 mg)
  7. additionadded
  8. stirringThe mixture was stirred at 20° C. for 3 hours
  9. customThe solvent was removed in vacuo
  10. dissolutionthe residue dissolved in ethyl acetate (50 ml)
  11. washwashed with water (50 ml) and brine (30 ml)
  12. dry with materialdried (MgSO4)
  13. customthe solvent removed in vacuo
  14. customPurification by chromatography on silica gel (Varian Bondelut cartridge)
  15. washeluting with cyclohexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-bfe287435269421eae45ec953271edc1
Source dataset
uspto-grants-2004_01
Patent number
US06677316B2

Reaction notes

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