Acetonitrile → Pravastatin

HRID 891027Notes

Reaction equation

HRID 891027 reaction equation
[OH-].[Na+].C(#N)C.[CH3:6][CH2:7][C@@H:8]([C:10]([O:12][C@@H:13]1[C@@H:18]2[C@@H:19]([CH2:24][CH2:25][C@@H:26]([OH:34])[CH2:27][C@@H:28]([OH:33])[CH2:29][C:30]([O-:32])=[O:31])[C@@H:20]([CH3:23])[CH:21]=[CH:22][C:17]2=[CH:16][C@@H:15]([OH:35])[CH2:14]1)=[O:11])[CH3:9].[Na+]>O>[CH3:6][CH2:7][C@@H:8]([C:10]([O:12][C@@H:13]1[C@@H:18]2[C@@H:19]([CH2:24][CH2:25][C@@H:26]([OH:34])[CH2:27][C@@H:28]([OH:33])[CH2:29][C:30]([OH:32])=[O:31])[C@@H:20]([CH3:23])[CH:21]=[CH:22][C:17]2=[CH:16][C@@H:15]([OH:35])[CH2:14]1)=[O:11])[CH3:9]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 16759173Pravastatin sodium

Product 1

HCID 54687PravastatinYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

The pH was raised to 8.5 by addition of 2M sodium hydroxide in water (1.2 ml) and the solution was heated to 50° C. Acetonitrile (90 ml) was added to the mixture and then the mixture was stirred at elevated temperature for one hour. The mixture was allowed to cool to 20–25° C. (“ambient temperature”), was held at ambient temperature for two hours and then cooled to 5° C. and maintained at 5° C. for 12 hours, whereupon pravastatin sodium crystallized. The crystals were then isolated by filtration and washed with acetonitrile (2×10 ml) and dried under vacuum at 50° C. X-ray diffraction analysis revealed the presence of Form A. Pravastatin Form A was obtained in 92% yield.

Workup

  1. temperatureto cool to 20–25° C. (“ambient temperature”)
  2. waitwas held at ambient temperature for two hours
  3. temperaturecooled to 5° C.
  4. customcrystallized
  5. customThe crystals were then isolated by filtration
  6. washwashed with acetonitrile (2×10 ml)
  7. customdried under vacuum at 50° C

Sources & evidence

ORD record
ord-0108cd5e40dc40eaa818e9ad9d74c339
Source dataset
uspto-grants-2006_02
Patent number
US07001919B2

Reaction notes

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