Water → Rosuvastatin

HRID 578743

Reaction equation

HRID 578743 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([NH-])CCC.O.C(N)CCC>CC(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 8007ButylamineHCID 86699893Rosuvastatin n-butylamide

Product 1

HCID 446157RosuvastatinYield 102.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

An autoclave having 800 cm3 is charged with 16.1 g (0.03 mol) rosuvastatin n-butylamide, 644 cm3 of water and 43.9 g (63.3 cm3; 0.60 mol) of n-butylamine. The reaction mixture is stirred at 120° C. for 24 hours, allowed to cool, diluted with 2-propanol at room temperature and evaporated in vacuo. The residue is boiled in ethylacetate, and while stirring, allowed to cool to room temperature. The crystals are filtered. Thus 14.8 g (89%) of rosuvastatin NBA salt are obtained. The crude salt is stirred in ethylacetate at room temperature, filtered, washed and dried. Thus dried product is boiled in ethylacetate, thereafter stirred in the same solvent at room temperature, filtered, washed and dried. Yield 9.32 g (56%) of rosuvastatin NBA salt, having purity (as determined by HPLC) exceeding 99.5%.

Workup

  1. temperatureto cool
  2. customevaporated in vacuo
  3. stirringwhile stirring
  4. temperatureto cool to room temperature
  5. filtrationThe crystals are filtered

Sources & evidence

ORD record
ord-b9f9d6028af0454a98728bba3a69a714
Source dataset
uspto-grants-2015_05
Patent number
US09040696B2

Linked notes

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