Uridine → HCID 69539450, compound

HRID 2416148Notes

Reaction equation

HRID 2416148 reaction equation
[Cl:1][C:2]1[CH:35]=[CH:34][C:5]([C:6]([C@@:8]2([OH:33])[C@@H:12]([CH2:13][O:14][C:15](=[O:23])[C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[O:11][C@@H:10](N3C=C(C)C(=O)NC3=O)[CH2:9]2)=O)=[CH:4][CH:3]=1.[C@@H:36]1([N:45]2C=CC(=O)NC2=O)[O:44][C@H](CO)[C@@H](O)[C@H]1O.C[N:54]1CCCCC1.[C:60]1([CH3:70])[CH:65]=CC(S(Cl)(=O)=O)=C[CH:61]=1.[OH2:71].[NH3:72]>C(#N)C.C(N(CC)CC)C>[Cl:1][C:2]1[CH:35]=[CH:34][C:5]([C:6]([C@@:8]2([OH:33])[C@@H:12]([CH2:13][O:14][C:15](=[O:23])[C:16]3[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=3)[O:11][C@@H:10]([N:72]3[CH:65]=[C:60]([CH3:70])[C:61]([NH2:54])=[N:45][C:36]3=[O:44])[CH2:9]2)=[O:71])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 6029Uridine2×HCID 73974-Toluenesulfonyl chlorideHCID 12291N-MethylpiperidineHCID 12896473Azane;hydrateHCID 69539432HCID 69539432, compound

Product 1

HCID 69539450HCID 69539450, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent

Procedure

To the suspension of 3.00 g of 3′,5′-O-bis(4-chlorobenzoyl)thymidine (a uridine derivative, where X is methyl group) in 15 mL of acetonitrile was added 0.85 mL (1.2 times moles based on the uridine derivative) of 1-methylpiperidine and 1.70 mL of triethylamine, and the resulting mixture was cooled. The solution of 2.31 g of p-toluenesulfonyl chloride in 15 ml of acetonitrile was added dropwise with keeping the temperature at 0° C. or below 0° C., and the mixture was stirred for 3 hours with keeping the temperature at 0° C. or below 0° C. With keeping the temperature at 0° C. or below 0° C., 15 ml of 28% ammonia water was added, and the mixture was stirred for 6hours. After the filtration of the solvent, 10 mL of methanol was added to the resulting residue, and the mixture was stirred for 2 hours with ice cooling. After the filtration of the solvent, the resulting solid was dried to give 1.59 g of 3′,5′-O-bis(4-chlorobenzoyl)-5-methyl-2′-deoxycytidine as a light brown solid. Yield 52%.

Workup

  1. additionwas added 0.85 mL (1.2 times moles
  2. temperaturethe resulting mixture was cooled
  3. customat 0° C. or below
  4. custom0° C.
  5. customat 0° C. or below
  6. custom0° C
  7. customat 0° C. or below
  8. additionwas added
  9. stirringthe mixture was stirred for 6hours
  10. filtrationAfter the filtration of the solvent, 10 mL of methanol
  11. additionwas added to the resulting residue
  12. stirringthe mixture was stirred for 2 hours with ice cooling
  13. filtrationAfter the filtration of the solvent
  14. customthe resulting solid was dried

Sources & evidence

ORD record
ord-9ae3a9ebc3dd4d0b843287e878fc0755
Source dataset
uspto-grants-2004_11
Patent number
US06822090B2

Reaction notes

Loading…