Uridine → HCID 69539402, compound

HRID 2416146Notes

Reaction equation

HRID 2416146 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([C:6]([C@@:8]2([OH:32])[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](N3C=CC(=O)NC3=O)C2)=[O:7])=[CH:4][CH:3]=1.[C@@H]1([N:44]2C=CC(=O)[NH:47][C:45]2=O)O[C@H](CO)[C@@H](O)[C@H]1O.N12[CH2:59][CH2:58][N:55]([CH2:56][CH2:57]1)[CH2:54]C2.C1(C)C=CC(S(Cl)(=O)=[O:67])=CC=1>C(N(CC)CC)C.C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C@@:8]2([OH:32])[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:58]([N:55]3[CH:56]=[CH:57][C:45]([NH2:47])=[N:44][C:54]3=[O:67])[CH2:59]2)=[O:7])=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 6029UridineHCID 73974-Toluenesulfonyl chlorideHCID 9237DabcoHCID 69539405HCID 69539405, compound

Product 1

HCID 69539402HCID 69539402, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To 2.0 g of 3′,5′-O-bis(4-chlorobenzoyl)-2′-deoxyuridine was added 60 mL of acetonitrile, 0.81 g of triethylamine, 0.54 g (1.2 times moles based on the uridine derivative) of 1,4-diazabicyclo[2.2.2]octane and 1.5 g of p-toluenesulfonyl chloride, and the resulting mixture was stirred at room temperature for 3 hours. Ammonia gas was bubbled into the reaction mixture at room temperature for 1 hour, and the mixture was stirred in an ice bath for 30 minutes. The crystals were filtered and washed with acetonitrile to give 1.52 g of 3′,5′-O-bis(4-chlorobenzoyl)-2′-deoxycytidine. Yield 75.2%.

Workup

  1. customAmmonia gas was bubbled into the reaction mixture at room temperature for 1 hour
  2. stirringthe mixture was stirred in an ice bath for 30 minutes
  3. filtrationThe crystals were filtered
  4. washwashed with acetonitrile

Sources & evidence

ORD record
ord-2fe7c47b59714efd95caa7d6974b9d68
Source dataset
uspto-grants-2004_11
Patent number
US06822090B2

Reaction notes

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