Abstract
AbstractFour new chiral α‐(nonafluoro‐tert‐butoxy)carboxylic acids were synthesized from naturally occurring α‐amino acids (alanine, valine, leucine and isoleucine, respectively), and tested in 1H‐ and 19F‐NMR experiments as chiral NMR shift reagents. The NMR studies were carried out at room temperature, using CDCl3 and C6D6 as solvents, and (RS)‐α‐phenylethylamine and (RS)‐α‐(1‐naphthyl)ethylamine as racemic model compounds. To demonstrate the applicability of the reagents, the racemic drugs ketamine and prasugrel were also tested.
Highlights
Since most of the active pharmaceutical ingredients (APIs) are optically active molecules, the pharmaceutical industry needs simple, fast and accurate analytical methods for determining enantiomeric ratios
NMR Spectroscopy offers an advantageous possibility for chiral discrimination,[6,7,8,9] because NMR instruments are usually available for routine structure determinations
We showed that α-(nonafluoro-tert-butoxy)carboxylic acids, based on lactic acid (R)-1, mandelic acid (RS)-2 and 3-phenyllactic acid (R)
Summary
Since most of the active pharmaceutical ingredients (APIs) are optically active molecules, the pharmaceutical industry needs simple, fast and accurate analytical methods for determining enantiomeric ratios. NMR Spectroscopy offers an advantageous possibility for chiral discrimination,[6,7,8,9] because NMR instruments are usually available for routine structure determinations. The ee determination by NMR spectroscopy is based on diastereomer formation, either as 1) derivatization in a separate step before the measurement, or 2) in situ complex formation (using lanthanide shift reagents or chiral solvating agents)
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