Background:
Cinacalcet is one of the second-generation calcimimetics which consists of a
chiral center. The pharmacological effect of R-cinacalcet is 1000 times greater than that of the Scinacalcet.
As mentioned in many literatures, 1-(1-naphthyl)ethylamine is used as the starting material
for the synthesis of cinacalcet. The absolute structure of cinacalcet is influenced by the starting materials.
Methods:
We present the chiral separation of cinacalcet and its starting material, 1-(1-naphthyl) ethylamine
along with one of its intermediates, N-(1-(naphthalen-1-yl) ethyl)-3- (3-(trifluoromethyl) phenyl)
propanamide by high-performance liquid chromatography with chiral stationary phase and chiral mobile
phase additives.
Results:
On vancomycin and cellulose tri 3,5-dimethylphenylcarbamate) chiral stationary phase, cinacalcet
and 1-(1-naphthyl)ethylamine achieved enantioseparation under normal phase with addition of
triethylamine additives, respectively. Meanwhile, 1-(1-naphthyl)ethylamine and N-(1-(naphthalen-1-
yl)ethyl)-3-(3-(trifluoromethyl) phenyl) propanamide achieved enantioseparation on 1-napthalene vancomycin
chiral stationary phase using D-tartaric acid, diethyl L-tartrate and diethyl D-tartrate as chiral
mobile phase additives.
Conclusion:
The chiral recognition in our experiment was based on the hydrogen-bonding, dipoledipole
and π-π interactions among the solutes, chiral stationary phases and chiral mobile phase additives.
In addition, the space adaptability of chiral stationary phases also affected the separation efficacy.
