Sodium Benzoate → HCID 20598835, compound

HRID 989429Notes

Reaction equation

HRID 989429 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@@:10]1([CH2:34][O:35]S(C)(=O)=O)[O:11][C@H:12]2[N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[NH:25][C:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:40]([O-])(=[O:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[Na+]>CN(C=O)C>[CH2:1]([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@@:10]1([CH2:34][O:35][C:40](=[O:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[O:11][C@H:12]2[N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[NH:25][C:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 517055Sodium BenzoateHCID 20598837HCID 20598837, compound

Product 1

HCID 20598835HCID 20598835, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

(1S,3R,4R,7S)-7-Benzyloxy-1-methanesulfonyloxymethyl-3-(6-N-benzoyl-adenine-9-yl)-2,5-dioxabicyclo-[2.2.1]heptane (5D) (11.5 g.; 20.8 mmol) was dissolved in anh. DMF (450 mL). Sodium benzoate (5.40 g.; 37.4 mmol) was added and the mixture was heated to 90° C. for 7 h. The solution was cooled to rt., filtered, evaporated and coevaporated with AcCN. The residue was redissolved in dichloromethane (150 mL) and a saturated aqueous solution of NaHCO3 (150 mL) was added. The phases were separated and the organic phase was washed with a saturated aqueous solution of NaHCO3 (2×100 mL) and brine (100 mL), dried (Na2SO4) and evaporated to give 12.5 g. of a yellowish solid. Recrystallization from EtOH:H2O (1250 mL; 1:1 v/v) gave 28 in 88% yield (10.63 g.). δH (DMSO-d6): 11.2 (1H, br s), 8.72 (1H, s), 8.48 (1H, s), 8.06 (2H, m), 7.94 (2H, m), 7.66 (2H, m), 7.54 (4H, m), 7.36-7.26 (5H, m), 6.11 (1H, s), 4.97 (1H, s), 4.82 (2H, s), 4.77 (1H, s), 4.75 (1H, d, J=12.4 Hz), 4.69 (1H, d, J=11.9 Hz), 4.19 (1H, d, J=8.0 Hz), 4.07 (1H, d, J=7.9 Hz). δc (DMSO-d6): 165.3, 150.5, 141.9, 137.7, 133.7, 132.5, 129.3, 129.1, 128.9, 128.6, 128.5, 128.3, 127.7, 127.6, 125.7, 85.9, 85.3, 77.9, 77.1, 72.0, 71.3, 60.6.

Workup

  1. temperatureThe solution was cooled to rt
  2. filtration, filtered
  3. customevaporated
  4. dissolutionThe residue was redissolved in dichloromethane (150 mL)
  5. additiona saturated aqueous solution of NaHCO3 (150 mL) was added
  6. customThe phases were separated
  7. washthe organic phase was washed with a saturated aqueous solution of NaHCO3 (2×100 mL) and brine (100 mL)
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customto give 12.5 g
  11. customRecrystallization from EtOH

Sources & evidence

ORD record
ord-b823dc0d6b3140108435e6f1ec947eba
Source dataset
uspto-grants-2003_10
Patent number
US06639059B1

Reaction notes

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