Process for the enantiomeric resolution of apremilast intermediates
OwnerRamesh Dandala, Sureshbabu Jayachandra +3inventors
InventorsRamesh Dandala, Sureshbabu Jayachandra, Vipin Kumar Kaushik, Nageshwara Rao Achanta, Sivaprasad Dorasala
Life of this patent
Estimating the term…
Abstract
A process for the resolution of racemic 2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulphonyl)-eth-2-ylamine using novel chiral salts is disclosed. An L-phenylalanine p-toluene-sulfonamide salt of (S)-2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulphonyl)-eth-2-ylamine and a di-p-toluoyl-L-tartaric acid salt of (S)-2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulphonyl)-eth-2-ylamine are also provided.
Claims4
A process for the preparation of (S)-2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulphonyl)-eth-2-ylamine, comprising the steps of:
- a. dissolving a racemic mixture of 2-(3-ethoxy-4-methoxyphenyl)-1-(methyl sulphonyl)-eth-2-ylamine in an organic solvent to form a solution;
- b. adding L-phenylalanine p-toluene sulfonamide to the solution;
- and
- c. isolating a L-phenylalanine p-toluene sulfonamide salt of (S)-2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulphonyl)-eth-2-ylamine,
- wherein the chiral salt of (S)-2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulphonyl)-eth-2-ylamine is further converted into apremilast.
A L-phenylalanine p-toluene-sulfonamide salt of (S)-2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulphonyl)-eth-2-ylamine.
Dependencies are inferred from the claim text.