Methane → HCID 10663046, compound

HRID 659839Notes

Reaction equation

HRID 659839 reaction equation
C([O:8][C@:9]12[C@@H:16]([CH2:17][O:18]CC3C=CC=CC=3)[O:15][C@@H:14]([N:26]3[CH:34]=[C:32]([CH3:33])[C:30](=[O:31])[NH:29][C:27]3=[O:28])[C@@:13]1([O:35][CH3:36])[O:12][CH2:11][CH2:10]2)C1C=CC=CC=1.C>CO.[OH-].[Pd+2].[OH-]>[OH:8][C@:9]12[C@@H:16]([CH2:17][OH:18])[O:15][C@@H:14]([N:26]3[CH:34]=[C:32]([CH3:33])[C:30](=[O:31])[NH:29][C:27]3=[O:28])[C@@:13]1([O:35][CH3:36])[O:12][CH2:11][CH2:10]2

Participants

5

Reactant 2

HCID 297MethaneHCID 10743796HCID 10743796, compound

Product 1

HCID 10663046HCID 10663046, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of nucleoside 16 (1.20 g, 2.43 mmol) in methanol (10 cm3) was added 20% palladium hydroxide over charcoal (250 mg) and the mixture was carefully degassed under reduced pressure. An atmosphere of hydrogen was applied and stirring was continued for 12 h. The catalyst was removed by filtration of the reaction mixture through a glass column (1×8 cm) packed with silica gel in methanol. The column was additionally washed with methanol (20 cm3). All fractions were collected, evaporated to dryness and co-evaporated with petroleum ether to yield a glass-like solid. This residue was purified by silica gel chromatography eluting with a gradient of 5-10% methanol in dichloromethane (v/v). The fractions containing the product were collected, combined and evaporated to dryness. The residue was dissolved in anhydrous methanol (5 cm3) and anhydrous benzene (100 cm3) was added. Lyophilisation yielded nucleoside 17 (0.61 g, 79%) as a white solid material. δH (CD3OD) 7.45 (1H, S, 6-H), 5.93 (1H, s, 1′-H), 4.15-3.81 (5H, m, 5-Ha, 5-Hb, 2″-Ha, 2″-Hb, 4′-H), 3.43 (3H, s, CH3—O), 2.47-2.40 (1H, m, 1″-Ha), 2.03-1.93 (1H, m, 1″-Hb), 1.92 (3H, s, CH3). δC (CD3OD) 164.1 (C-4), 150.1 (C-2), 138.3 (C-6), 109.6 (C-5), 108.3 (C-2′), 84.4, 84.1, 82.4 (C-1′, C-3′, C-4′), 68.0, 59.5 (C-5′, C-2″), 49.6 (CH3—O), 34.0 (C-1″), 10.5 (CH3). FAB-MS m/z 315.13 [M+H]+, 337.09 [M+Na]+ (Found: C, 49.9; H, 5.7; N, 8.2; C13H18O7N2 requires C, 49.7; H, 5.8; N, 8.9%).

Workup

  1. customthe mixture was carefully degassed under reduced pressure
  2. customThe catalyst was removed by filtration of the reaction mixture through a glass column (1×8 cm)
  3. washThe column was additionally washed with methanol (20 cm3)
  4. customAll fractions were collected
  5. customevaporated to dryness and co-evaporated with petroleum ether
  6. customto yield a glass-like solid
  7. customThis residue was purified by silica gel chromatography
  8. washeluting with a gradient of 5-10% methanol in dichloromethane (v/v)
  9. additionThe fractions containing the product
  10. customwere collected
  11. customevaporated to dryness
  12. dissolutionThe residue was dissolved in anhydrous methanol (5 cm3)
  13. additionanhydrous benzene (100 cm3) was added

Sources & evidence

ORD record
ord-245b8ad1a37547bb8cb71e8044aa6fec
Source dataset
uspto-grants-2011_12
Patent number
US08080644B2

Reaction notes

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