Water → AZT Malonic Acid

HRID 1869220Notes

Reaction equation

HRID 1869220 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 86585369AZT Malonic AcidYield 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-6c716e08ef2a4dfd8074701477ed9f18
Source dataset
uspto-grants-2009_12
Patent number
US07638528B2

Reaction notes

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