Potassium Carbonate → N4-Benzoyl-1-tert-butyloxycarbonylmethylcytosine

HRID 54621Notes

Reaction equation

HRID 54621 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[C:10]([NH:18][C:19]1[CH:24]=[CH:23][NH:22][C:21](=[O:25])[N:20]=1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:10]([NH:18][C:19]1[CH:24]=[CH:23][N:22]([CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[C:21](=[O:25])[N:20]=1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 178522337HCID 178522337, compound

Product 1

HCID 22101730N4-Benzoyl-1-tert-butyloxycarbonylmethylcytosine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl bromoacetate (24 ml; 0.15 mol) is slowly added dropwise, at room temperature, to a suspension of N4 -benzoylcytosine (21.5 g; 0.1 mol) and potassium carbonate 13.8 g; 0.1 mol) in anhydrous N,N-dimethylformamide (2.15 l). The heterogeneous mixture is stirred vigorously at room temperature for 20 h and insoluble starting material is subsequently filtered off with suction; the filtrate is concentrated in vacuo and the residue is subsequently distilled repeatedly with toluene and then taken up in chloroform (1.0 l); it is then extracted once by shaking with water (0.3 l), and the phases are swiftly separated. The organic phase is filtered once more and concentrated. Yield: 15.23.g (46%).

Workup

  1. filtrationis subsequently filtered off with suction
  2. concentrationthe filtrate is concentrated in vacuo
  3. distillationthe residue is subsequently distilled repeatedly with toluene
  4. extractionit is then extracted once
  5. stirringby shaking with water (0.3 l)
  6. customthe phases are swiftly separated
  7. filtrationThe organic phase is filtered once more
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-502d8aacb5dc4b6d8870e5b87a397057
Source dataset
uspto-grants-1997_04
Patent number
US05623049

Reaction notes

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