Pyridine → HCID 21903610, compound

HRID 650682Notes

Reaction equation

HRID 650682 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:7][CH:8]([Cl:12])[C:9]([OH:11])=[O:10]>ClCCl>[Cl:7][CH:8]([Cl:12])[C:9]([O-:11])=[O:10].[NH+:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 6597Dichloroacetic Acid

Product 1

HCID 21903610HCID 21903610, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridinium dichloroacetate was prepared in situ by addition of 1.3 equivalents of pyridine (0.49 mL, 6.07 mmol) to dry dichloromethane (4 mL) followed by addition of 1.2 eq. of dichloroacetic acid (0.46 mL, 5.60 mmol). To this mixture was added bisamidite reagent (1.78 mL, 5.60 mmol) followed by the dropwise addition of 2′-deoxy-5′-O-DMT-4-N-benzoylcytidine (2.97 g, 4.67 mmol) dissolved in dry dichloromethane (6 mL). The reaction mixture was stirred under argon at ambient temperature for 2 hours and transferred directly to the top of a short silica gel column. The amidite product was eluted with 70% tOAc/hexanes (1% triethylamine). The appropriate fractions ere collected and evaporated to give 3.47 g (89%) of the title compound as a white foam. 31P NMR (CDCl3) δ 149.29, 149.88.

Workup

  1. washThe amidite product was eluted with 70% tOAc/hexanes (1% triethylamine)
  2. customThe appropriate fractions ere collected
  3. customevaporated

Sources & evidence

ORD record
ord-5b1cbe36a44342c5bd4d11811d63ca11
Source dataset
uspto-grants-2001_08
Patent number
US06274725B1

Reaction notes

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