Stavudine DMPU → Stavudine

HRID 913262

Reaction equation

HRID 913262 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>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

3

Reactant 1

HCID 86625622Stavudine DMPU

Product 1

HCID 18283StavudineYield 98.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Stavudine DMPU solvate (25 g, 0.060 mole) is dissolved in isopropanol (250 ml), and treated with activated carbon anti-eno crowns (2.5 g) at reflux temperature. Reaction mass is filtered while hot and washed with hot isopropanol (25 ml). The combined filtrate and wash are concentrated to 100 ml and allowed the mass to cool to room temperature slowly. Cooled the mass to 0-5° C. and the precipitated product is filtered. washed the product with chilled isopropanol (10 ml) and air dried to give 13.2 g (83%) of the title compound which purity greater than 99%. XRD data resembles crystalline form-I

Workup

  1. additiontreated with activated carbon anti-eno crowns (2.5 g)
  2. temperatureat reflux temperature
  3. customReaction mass
  4. filtrationis filtered while hot and
  5. washwashed with hot isopropanol (25 ml)
  6. washThe combined filtrate and wash
  7. concentrationare concentrated to 100 ml
  8. temperatureCooled the mass to 0-5° C.
  9. filtrationthe precipitated product is filtered
  10. washwashed the product with chilled isopropanol (10 ml) and air
  11. customdried

Sources & evidence

ORD record
ord-704beaa106dd4e47b01acf396000f4ad
Source dataset
uspto-grants-2011_09
Patent number
US08026356B2

Linked notes

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