Water → Rosuvastatin

HRID 578742Notes

Reaction equation

HRID 578742 reaction equation
[CH3:1][CH:2]([C:4]1[N:9]=[C:8]([N:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH3:11])[N:7]=[C:6]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[C:5]=1/[CH:23]=[CH:24]/[C@@H:25]([OH:33])[CH2:26][C@@H:27]([OH:32])[CH2:28][C:29]([OH:31])=[O:30])[CH3:3].C[N-]C.O.C(N)(C)(C)C>C(O)C>[CH3:3][CH:2]([C:4]1[N:9]=[C:8]([N:10]([S:12]([CH3:15])(=[O:13])=[O:14])[CH3:11])[N:7]=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[C:5]=1/[CH:23]=[CH:24]/[C@@H:25]([OH:33])[CH2:26][C@@H:27]([OH:32])[CH2:28][C:29]([OH:31])=[O:30])[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 6385Tert-ButylamineHCID 86699894HCID 86699894, compound

Product 1

HCID 446157RosuvastatinYield 103.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

Method “A”: An autoclave having 50 cm3 volume is charged with 0.89 g (1.75 mmol) of rosuvastatin N,N-dimethylamide, 35.6 cm3 of water and 2.56 g (3.7 cm3; 3.5 mmol) tert-butylamine. The reaction mixture is stirred at 120° C. for 16 hours. The mixture is allowed to cool to room temperature, the reaction mixture is diluted with ethanol in portions and evaporated in vacuo. The evaporation residue is stirred in a mixture of tert-butylmethylether and heptane (2:5 v/v, 4 cm3) and the crystals are filtered. Thus 0.87 g (90%) of rosuvastatin TBA salt are obtained. The crude salt is recrystallized from acetonitrile/2-propanol. Yield, 0.58 g (60%) rosuvastatin TBA salt having purity (by HPLC) exceeding 99.5%.

Workup

  1. temperatureto cool to room temperature
  2. customevaporated in vacuo
  3. stirringThe evaporation residue is stirred in a mixture of tert-butylmethylether and heptane (2:5 v/v, 4 cm3)
  4. filtrationthe crystals are filtered

Sources & evidence

ORD record
ord-ebdecd3099f54a1eacadc28ded7e1422
Source dataset
uspto-grants-2015_05
Patent number
US09040696B2

Reaction notes

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