Benzoyl chloride → HCID 86638037, compound

HRID 1399507Notes

Reaction equation

HRID 1399507 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-3254ddd476bb43d4a1cf94973703e22b
Source dataset
uspto-grants-2014_12
Patent number
US08906880B2

Reaction notes

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