Water → Stavudine

HRID 913266

Reaction equation

HRID 913266 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.CN1C(=O)N(C)CCC1.O>C(O)(C)C>[C@@H:10]1([N:4]2[CH:3]=[C:2]([CH3:1])[C:8](=[O:9])[NH:7][C:5]2=[O:6])[O:14][C@H:13]([CH2:15][OH:16])[CH:12]=[CH:11]1

Participants

4

Reactant 2

HCID 962WaterHCID 86625622HCID 86625622, compound

Product 1

HCID 18283StavudineYield 88.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
2.5 °C

Procedure

Stavudine-DMPU solvate (25 g, 0.07 moles), water (5 g) and isopropanol (250 ml) are heated to about 82° C. to get clear colorless solution. Heating is continued so as to distill the solution at atmospheric pressure until about 80 ml of isopropanol remained in side. The solution is allowed to cool on its own. The mixture is further cooled to 0-5° C. for 1.5 hrs. The precipitated product is filtered, washed with isopropanol (2×10 ml) and air dried to give 13.9 g (87.2%) of pure white crystalline Stavudine. The HPLC results are given in Table 2.

Workup

  1. customto get clear colorless solution
  2. temperatureHeating
  3. distillationto distill the solution at atmospheric pressure until about 80 ml of isopropanol
  4. temperatureto cool on its own
  5. filtrationThe precipitated product is filtered
  6. washwashed with isopropanol (2×10 ml) and air
  7. customdried

Sources & evidence

ORD record
ord-617fba8be3594a8fbcccd47e91e8e6a7
Source dataset
uspto-grants-2011_09
Patent number
US08026356B2

Linked notes

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