Process for resolving alanine, 3-fluoro and 2-deutero-3-fluoro-DL-alanine
AssigneeMerck & Co., Inc.
InventorsJohn M. Chemerda, George Gal
Life of this patent
Estimating the term…
Abstract
DL-Alanine, 3-fluoro-DL-alanine and 2-deutero-3-fluoro-DL-alanine, are resolved by reaction with a resolving base and a .beta.-dicarbonyl compound. The resulting azomethine diastereomeric salts which are easily separated, the masking group is readily removed under mildly acidic conditions.
Claims5
The process for resolving a DL-mixture of an alanine compound which is alanine, 3-fluoroalanine, or 2-deutero-3-fluoro alanine which comprises reacting approximately equimolar amounts of the alanine compound, a resolving base which is quinine, quinidine, brucine, strychnine, d-.alpha.,N,N-trimethylbenzylamine, or 1-.alpha.,N,N-trimethylbenzylamine, and a .beta.-dicarbonyl compound of the formula ##STR2## wherein R is methyl, phenyl or alkoxy of 1-5 carbon atoms, in a solution of a lower alkanol of 1-5 carbon atoms at reflux for 1/2-3 hours, and separating the salt parts of the diastereomers by crystallization, then treating both separately, first with an alkali metal hydroxide, then with H.sub.3 O.sup.+, and recovering the respective individual isomers.
Dependencies are inferred from the claim text.