Benzoyl chloride → HCID 86638037, compound

HRID 2424338Notes

Reaction equation

HRID 2424338 reaction equation
[F:1][C@:2]1([CH3:18])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]1=[O:12].[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>N1C=CC=CC=1>[C:19]([NH:15][C:14]1[CH:16]=[CH:17][N:10]([C@@H:3]2[O:4][C@H:5]([CH:8]([C:19](=[O:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[OH:9])[C@@:6]([C:19](=[O:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([OH:7])[C@:2]2([F:1])[CH3:18])[C:11](=[O:12])[N:13]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 64812362'-Deoxy-2'-fluoro-2'-c-methylcytidine

Product 1

HCID 86638037HCID 86638037, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

2′-Deoxy-2′-fluoro-2′-C-methylcytidine (1.0 g, 1 eq) (Clark, J., et al., J. Med. Chem., 2005, 48, 5504-5508) was dissolved in 10 ml of anhydrous pyridine and concentrated to dryness in vacuo. The resulting syrup was dissolved in 20 ml of anhydrous pyridine under nitrogen and cooled to 0° C. with stirring. The brown solution was treated with benzoyl chloride (1.63 g, 3 eq) dropwise over 10 min. The ice bath was removed and stirring continued for 1.5 h whereby thin-layer chromatography (TLC) showed no remaining starting material. The mixture was quenched by addition of water (0.5 ml) and concentrated to dryness. The residue was dissolved in 50 mL of dichloromethane (DCM) and washed with saturated NaHCO3 aqueous solution and H2O. The organic phase was dried over NaSO4 and filtered, concentrated to dryness to give N4, 3′,5′-tribenzoyl-2′-Deoxy-2′-fluoro-2′-C-methylcytidine (2.0 g, Yield: 91%).

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. dissolutionThe resulting syrup was dissolved in 20 ml of anhydrous pyridine under nitrogen
  3. customThe ice bath was removed
  4. stirringstirring
  5. customThe mixture was quenched by addition of water (0.5 ml)
  6. concentrationconcentrated to dryness
  7. dissolutionThe residue was dissolved in 50 mL of dichloromethane (DCM)
  8. washwashed with saturated NaHCO3 aqueous solution and H2O
  9. dry with materialThe organic phase was dried over NaSO4
  10. filtrationfiltered
  11. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e86c1a610dd14e728b636063dc8e860d
Source dataset
uspto-grants-2011_06
Patent number
US07964580B2

Reaction notes

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