Water → Simvastatin

HRID 2244857Notes

Reaction equation

HRID 2244857 reaction equation
[CH3:1][CH2:2][C:3]([C:6]([O:8][C@@H:9]1[C@@H:14]2[C@@H:15]([CH2:20][CH2:21][C@@H:22](O)[CH2:23][C@@H:24]([OH:29])[CH2:25][C:26]([O-:28])=[O:27])[C@@H:16]([CH3:19])[CH:17]=[CH:18][C:13]2=[CH:12][C@H:11]([CH3:31])[CH2:10]1)=O)([CH3:5])[CH3:4].[NH4+].S([O-])(O)(=O)=O.[K+].[OH2:39]>C(#N)C>[CH3:1][CH2:2][C:3]([C:6]([O:8][C@@H:9]1[C@@H:14]2[C@@H:15]([CH2:20][CH2:21][C@H:22]3[O:28][C:26](=[O:27])[CH2:25][C@H:24]([OH:29])[CH2:23]3)[C@@H:16]([CH3:19])[CH:17]=[CH:18][C:13]2=[CH:12][C@H:11]([CH3:31])[CH2:10]1)=[O:39])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 962Water2×HCID 516920Potassium bisulfateHCID 10961424Simvastatin ammonium salt

Product 1

HCID 54454Simvastatin

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
42.5 °C

Procedure

Simvastatin ammonium salt (25 g) was taken in acetonitrile (100 ml) under nitrogen atmosphere. To the reaction mixture, potassium hydrogen sulfate (18.7 g) taken in water (50 ml) was added. The reaction mixture was stirred for 3-4 hours at 40-45° C. Water (250 ml) was added to the reaction mixture under stirring. The resulting lactonized product obtained was filtered and washed with water, dried under vacuum to yield crude simvastatin. The crude simvastatin was recrystallized from methanol and water to obtain pure simvastatin.

Workup

  1. additionwas added
  2. stirringunder stirring
  3. customThe resulting lactonized product obtained
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried under vacuum
  7. customto yield crude simvastatin
  8. customThe crude simvastatin was recrystallized from methanol and water

Sources & evidence

ORD record
ord-376b52bd2f8648b89bd96a3aae34c74c
Source dataset
uspto-grants-2010_03
Patent number
US07678927B2

Reaction notes

Loading…