Determination Of E.e.value Of Aliphatic Chiral Amines

The chiral aliphatic amine compounds are common compounds of the active pharmaceutical indegrients and intermediates,however due to the UV absorption of these compounds is generally weak,so determination the chiral amino aliphatic ee value determination method has important significance.It is a common HPLC method to use aliphatic amines as aromatic amines.One,the samples that derivatized by conventional derivatization reagent,and the UV absorption was enhanced,was detected with the chiral column,for example3-Aminopiperidine and 2-Aminobutane.The product of 3-Aminopiperidine and benzoyl chloride was detected by HPLC-UV with CHIRAL-AGP column at 254 nm,0.8 m L/min,30 ℃.The single reaction product of 3-Aminopiperidine with benzoyl chloride was detected,with the mobile phase of isopropyl alcohol-15 mol KH2PO4(2:98 by vol).Retention times: the(S)-enantiomer 7.15 min,the(R)-enantiomer 9.910 min.3-Aminopiperidine and benzoyl chloride double substitution reaction was detected,eluent:8% acetonitrile-92%15 mmol/L KH2PO4(pH=6.5).Retention times: the(S)-enantiomer37.967 min,the(R)-enantiomer 23.047 min.The enantiomeric excess of the product of2-Aminobutane and benzoyl chloride was determined by HPLC-UV using a ChromTech CHIRAL-AGP column.Analytical conditions for the HPLC were as follows,eluent: 2%isopropyl alcohol+98% KH2PO4(pH=6.0),detected at 254 nm.Retention times: the(S)-enantiomer 2.793 min,the(R)-enantiomer 5.445 min.Two,the chiral derivatization reagent was used for the samples,and the enantiomers were converted into diastereoisomers,then they can be detected with the general chromatographic column,for example 3-Aminobutanol and 2-Aminobutanol.The derivatives of 3-Aminobutanol and 2-Aminobutanol was detected by HPLC-UV with C18 column at 254 nm,0.8 mL/min,30 ℃.The reaction product of 3-Aminobutanol with(R)-1-methyl-2-naphthaleneacetyl chloride was detected,eluent: 40% acetonitrile +60%NaH2PO4(0.1%,pH=4.5).Retention times: the(S)-enantiomer 7.662 min,the(R)-enantiomer 5.747 min.The reaction product of 3-Aminobutanol with(R)-1-phenyl sulfonyl chloride was detected,eluent: 80% acetonitrile + 20% water.Retention times: the(S)-enantiomer 3.172 min,and the(R)-enantiomer 2.652 min.The reaction product of2-Aminobutanol with(R)-1-methyl-2-naphthaleneacetyl chloride was detected,eluent:80% methanol +20% HCl(c=0.2 mol/L).Retention times: the(S)-enantiomer 6.123 min,and the(R)-enantiomer 4.143 min.The reaction product of 2-Aminobutanol with(R)-1-phenyl sulfonyl chloride was detected,eluent: 70% methanol + 30% CH3COONa(c=50 mmol/L).Retention times: the(R)-enantiomer 6.538 min,the(S)-enantiomer 11.356 min.Method for the determination of 2-Aminobutanol e.e..The enantiomeric excess of Valine was determined by HPLC-UV using a SUMICHIRAL OA-6100.Analytical conditions for the HPLC were as follows: eluent: 2mmol/L CuSO4,0.8 mL/min,detected at 220 nm,30 ℃.Retention times: the D-valine4.415 min,the L-valine 13.770 min.