Uridine → HCID 69539402, compound

HRID 2416144Notes

Reaction equation

HRID 2416144 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.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[C@@H]1([N:55]2C=CC(=O)[NH:58][C:56]2=O)O[C@H](CO)[C@@H](O)[C@H]1O.[OH2:63].N.[CH2:65]([N:67]([CH2:70][CH3:71])[CH2:68][CH3:69])C>CN(C1C=CN=CC=1)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:68]([N:67]3[CH:70]=[CH:71][C:56]([NH2:58])=[N:55][C:65]3=[O:63])[CH2:69]2)=[O:7])=[CH:33][CH:34]=1

Participants

8

Reactant 5

HCID 6029UridineHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 12896473Azane;hydrateHCID 69539405HCID 69539405, compound

Product 1

HCID 69539402HCID 69539402, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

The method given in the conventional method (2) using DMAP was examined. The results are as follows. To 0.283 g of 3′,5′-O-bis(4-chlorobenzoyl)-2′-deoxyuridine was added 8.5 mL of acetonitrile, 0.221 g of p-toluenesulfonyl chloride, and 0.141 g (2.1 moles base on the uridine derivative) of DMAP, followed by adding dropwise 0.117 g of triethylamine, and the resulting mixture was stirred at room temperature for 22 hours. To this, 5.7 mL of 28% ammonia water was added and the mixture was stirred at room temperature for 2 hours, and then ice-cooled. Crystals were filtered and washed with 60% acetonitrile in water to give 0.17 g of 3′,5′-O-bis(4-chlorobenzoyl)-2′-deoxycytidine. Yield 60%.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. temperatureice-cooled
  3. filtrationCrystals were filtered
  4. washwashed with 60% acetonitrile in water

Sources & evidence

ORD record
ord-3a2aa8665e4b4626a48ad70d994ff2ee
Source dataset
uspto-grants-2004_11
Patent number
US06822090B2

Reaction notes

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