Cytidine → HCID 14862337, compound

HRID 1089311Notes

Reaction equation

HRID 1089311 reaction equation
[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[C:18]([O:22][CH3:23])(=[O:21])[CH:19]=[CH2:20]>CO.[Pd](Cl)Cl.[Li]>[CH3:23][O:22][C:18](/[CH:19]=[CH:20]/[C:16]1[C:14]([NH2:15])=[N:13][C:11](=[O:12])[N:10]([CH:17]=1)[C@@H:1]1[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3])=[O:21]

Participants

5

Reactant 2

HCID 6175CytidineHCID 7294Methyl Acrylate

Product 1

HCID 14862337HCID 14862337, compound

Reagents, catalysts & solvents 2

HCID 86739173HCID 86739173, compoundCatalystHCID 887MethanolSolvent2×

Procedure

A suspension of 19.1 g of 5-chloromercuriccytidine (b) in 150 ml of methanol was prepared and then 210 ml of a methanol solution of 0.1 M lithium palladium chloride (Li2PdCl4), 40 ml of methyl acrylate, and 4.12 g of cupric chloride were added to above suspension and the mixture was stirred at room temperature for 14 hours. The palladium precipitate was removed by filtration and hydrogen sulfide was bubbled into the filtrate and the formed precipitate was removed by Celite filtration. The filtrate was neutralized with a saturated sodium bicarbonate solution and evaporated to dryness under reduced pressure. The residue was recrystallized from aqueous solution to give 4.62 g of (E)-5-(2-methoxycarbonyl ethenyl) cytidine (c).

Workup

  1. customwas prepared
  2. customThe palladium precipitate was removed by filtration and hydrogen sulfide
  3. customwas bubbled into the filtrate
  4. customthe formed precipitate was removed by Celite filtration
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was recrystallized from aqueous solution

Sources & evidence

ORD record
ord-66923d3f71b548f081ec44b15ed60021
Source dataset
uspto-grants-1990_10
Patent number
US04965350

Reaction notes

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