Water → HCID 86585369, compound

HRID 1795366Notes

Reaction equation

HRID 1795366 reaction equation
[CH3:1][C:2]1[C:8](=[O:9])[NH:7][C:5](=[O:6])[N:4]([C@@H:10]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:12]([N:17]=[N+:18]=[N-:19])[CH2:11]2)[CH:3]=1.[C:20](Cl)(=[O:25])[CH2:21][C:22](Cl)=[O:23].[OH2:27]>C(#N)C>[CH3:1][C:2]1[C:8](=[O:9])[NH:7][C:5](=[O:6])[N:4]([C@@H:10]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:12]([N:17]=[N+:18]=[N-:19])[CH2:11]2)[CH:3]=1.[C:20]([OH:25])(=[O:6])[CH2:21][C:22]([OH:23])=[O:27]

Participants

5

Reactant 3

HCID 962WaterHCID 35370ZidovudineHCID 74269Propanedioyl dichloride

Product 1

HCID 86585369HCID 86585369, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

One gram of AZT was dissolved in 30 ml of anhydrous acetonitrile and added dropwise to a solution of 632 mg of malonyl chloride in 20 ml of acetonitrile at 0° C. The reaction mixture was stirred for 2 hours at 0° C. then at 8-10° C. for 4.5 hours. Thin layer chromatography was used to indicate that the reaction was complete. Water (4 ml) was added. Solvents were removed in vacuo and the residue purified by silica gel chromatography eluting with CHCl3:MeOH. Pure product was obtained in a 68% yield.

Workup

  1. waitat 8-10° C. for 4.5 hours
  2. customSolvents were removed in vacuo
  3. customthe residue purified by silica gel chromatography
  4. washeluting with CHCl3
  5. customPure product was obtained in a 68% yield

Sources & evidence

ORD record
ord-802d3519e8e244eda33c623a124f4d2b
Source dataset
uspto-grants-2006_04
Patent number
US07026469B2

Reaction notes

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