Water → Stavudine

HRID 988756Notes

Reaction equation

HRID 988756 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.CC(N(C)C)=O.O>CC(C)=O>[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

Participants

4

Reactant 2

HCID 962WaterHCID 11722976Stavudine DMA

Product 1

HCID 18283StavudineYield 76%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
500 °C

Procedure

The Stavudine-DMA solvate (15.2 g, 0.0488 mole) was combined with water (2.74 g) and acetone (220 mL) and heated to 500° C. when only a few grains of solid remained. The hot solution was filtered to remove the remaining solid, the filtrate was distilled until about 55 mL of acetone remained. The solution was allowed to cool on its own and at about 35-40° C. it was seeded with pure Stavudine. After 70 minutes of cooling on its own it was placed on an ice-water bath for one hour. The mixture was filtered, washed with acetone (2×11 mL) and air dried to give 8.32 g (0.0371 mole, 76.0%) of pure white Stavudine. The HPLC results are given in Table 2.

Workup

  1. filtrationThe hot solution was filtered
  2. customto remove the remaining solid
  3. distillationthe filtrate was distilled until about 55 mL of acetone
  4. temperatureto cool on its own
  5. customat about 35-40° C.
  6. temperatureAfter 70 minutes of cooling on its own it
  7. filtrationThe mixture was filtered
  8. washwashed with acetone (2×11 mL) and air
  9. customdried

Sources & evidence

ORD record
ord-3f9296b71e4f471ba5ca92134763fa28
Source dataset
uspto-grants-2003_10
Patent number
US06635753B1

Reaction notes

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