tert-Butyl rosuvastatin Chemical Properties

Melting point:

136-138oC

Boiling point:

704.2±70.0 °C(Predicted)

Density 

1.259

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly, Heated)

form 

Solid

pka

13.38±0.20(Predicted)

color 

White to Off-White

optical activity

Consistent with structure

Stability:

Hygroscopic

InChIKey

IJHZGLLGELSZAF-OKLSWEBGSA-N

SMILES

C(OC(C)(C)C)(=O)C[C@H](O)C[C@H](O)/C=C/C1=C(C(C)C)N=C(N(C)S(C)(=O)=O)N=C1C1=CC=C(F)C=C1

CAS DataBase Reference

355806-00-7(CAS DataBase Reference)

tert-Butyl rosuvastatin Usage And Synthesis

Uses

Rosuvastatin tert-Butyl Ester, is a metabolite of Rosuvastatin (R700500) a selective, competitive HMG-CoA reductase inhibitor.

Uses

tert-Butyl Rosuvastatin is an impurity of Rosuvastatin (287714-41-4 #CAS), which is a HMG-?CoA reductase inhibitor. In combination of pemafibrate or a salt, it can function as cardiovascular disease medication.

Synthesis

To a 500 ml flask equipped with a nitrogen blower and a mechanical stirrer was added the precursor compound of unsaturated carbonyls (18.60 g), tetrahydrofuran (40.5 ml) and methanol (11.5 ml) and the resulting suspension was stirred at room temperature to give a clear solution. To a 1000 ml three-necked flask equipped with a mechanical stirrer and a nitrogen blower, tetrahydrofuran (232 ml) and methanol (66.5 ml) were added to form a mixture. NaBH4 (2.22 g, 2.7 eq.) was then added, Methoxy-9-BBN (24 mL, 1.1 eq.) was added, and the mixture was stirred at -78??C for 10 min, then the tetrahydrofuran solution of the precursor compounds described above was added dropwise to the Methoxy-9-BBN mixture over a period of 1.5 h, and the reaction mixture was further stirred at -78??C for for 1 hour. H2O2 (9.3 mL, 30%) was then added and the reaction mixture was allowed to come to room temperature. Ethyl acetate (58 mL) and NH4Cl (174 mL) were slowly added to the reaction mixture under stirring at room temperature, the two phases were separated and separated by filtration. The organic phase was washed with saturated Na2SO3 (solution 46 mL) followed by H2O (116 mL), NaCl (116 mL) and then the organic phase was evaporated to dryness to obtain the target product tert-butyl resuvastatin.

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