Stavudine → Stavudine DMA

HRID 988753Notes

Reaction equation

HRID 988753 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])[CH:12]=[CH:11]2)[CH:3]=1.[CH3:17][N:18]([CH3:22])[C:19](=[O:21])[CH3:20]>C(O)(C)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])[CH:12]=[CH:11]2)[CH:3]=1.[CH3:20][C:19]([N:18]([CH3:22])[CH3:17])=[O:21]

Participants

4

Reactant 2

HCID 18283StavudineHCID 31374Dimethylacetamide

Product 1

HCID 11722976Stavudine DMAYield 75.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
79 °C

Procedure

Crude slightly beige Stavudine (17.25 g, 96.02% pure, 0.0739 mole) was combined with N,N-dimethylacetamide (25.91 g, 1.5 parts) and isopropanol (52 mL, 3 volumes) and heated to 79° C. when all solids dissolved. The cloudy mixture was filtered through dicalite and washed with isopropanol (12.5 mL). The filtrate was initially concentrated at atmospheric pressure and then a slight vacuum was applied so that the distillation occurred at 60-70° C. It was estimated that about 1.7 g of isopropanol remained. The solution was cooled, filtered, washed and dried to give 17.30 g of Stavudine-DMA solvate (0.0556 mol, 75.2%) with a chromatographic purity of 99.59%.

Workup

  1. dissolutiondissolved
  2. filtrationThe cloudy mixture was filtered through dicalite
  3. washwashed with isopropanol (12.5 mL)
  4. concentrationThe filtrate was initially concentrated at atmospheric pressure
  5. distillationa slight vacuum was applied so that the distillation
  6. customoccurred at 60-70° C
  7. temperatureThe solution was cooled
  8. filtrationfiltered
  9. washwashed
  10. customdried

Sources & evidence

ORD record
ord-85d782a8316240bfb7eff0e710170867
Source dataset
uspto-grants-2003_10
Patent number
US06635753B1

Reaction notes

Loading…