Potassium Carbonate → Brivudine

HRID 552063Notes

Reaction equation

HRID 552063 reaction equation
C(/[CH:4]=[CH:5]/[C:6]1[C:7](=[O:21])[NH:8][C:9](=[O:20])[N:10]([CH:19]=1)[C@@H:11]1[O:18][C@H:15]([CH2:16][OH:17])[C@@H:13]([OH:14])[CH2:12]1)(O)=O.C([O-])([O-])=O.[K+].[K+].[Br:28]N1C(=O)CCC1=O>CN(C)C=O>[Br:28]/[CH:4]=[CH:5]/[C:6]1[C:7](=[O:21])[NH:8][C:9](=[O:20])[N:10]([CH:19]=1)[C@@H:11]1[O:18][C@H:15]([CH2:16][OH:17])[C@@H:13]([OH:14])[CH2:12]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 10125531HCID 10125531, compound

Product 1

HCID 446727BrivudineYield 89,681.602%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-5-(2-carboxyvinyl)-2′-deoxyuridine (5.777 g, 19.37 mmol) in dimethylforamide (29 mL) was added K2CO3 (5.890 g, 42.61 mmol) and the suspension stirred at room temperature for 15 mins. A solution of N-bromosuccinimide (3.655 g, 20.53 mmol) was added dropwise over 30 mins at 20° C. The resulting suspension was filtered and the solid washed with DMF. The combined filtrate and washings were evaporated to dryness in vacuo and the residue dissolved in MeOH. To this silica gel was added and the suspension evaporated to dryness and the solid applied to the top of chromatographic column. The column was eluted with chloroform/methanol 92/8 to give a white solid (5787 g, 71.9%). Crystallisation from water gave a white powder.

Workup

  1. filtrationThe resulting suspension was filtered
  2. washthe solid washed with DMF
  3. customThe combined filtrate and washings were evaporated to dryness in vacuo
  4. dissolutionthe residue dissolved in MeOH
  5. additionTo this silica gel was added
  6. customthe suspension evaporated to dryness
  7. washThe column was eluted with chloroform/methanol 92/8

Sources & evidence

ORD record
ord-46b8299ca7e74eaf8ad7057c3e3da985
Source dataset
uspto-grants-2011_05
Patent number
US07951787B2

Reaction notes

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