L-Pyroglutamic Acid → HCID 178428120, compound

Participants

Reaction Steps

To a solution of (±)-7-(2,5-dichlorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline (2.3 g) in ethanol (10 ml) was added a solution of L-pyroglutamic acid (0.81 g) in ethanol (5 ml) at 80° C., and the mixture was gradually cooled to room temperature and stirred for 6 hours. The resulting crystals were filtered and washed with ethanol to give (+)-7-(2,5-dichlorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline L-pyroglutamate (1.61 g). Said crystals were recrystallized from ethanol and suspended in methanol, and to the suspension was added a solution of 28% sodium methoxide in methanol (0.5 g). Under reduced pressure, the solvent was evaporated. The resulting crystals were washed with water, dried, recrystallized from acetonitrile and dissolved in ethanol (10 ml). To the solution was added methanesulfonic acid (0.12 g), and the mixture was concentrated. The resulting crystals were recrystallized from ethanol to give (+)-7-(2,5-dichlorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline methanesulfonate (Compound 141) (0.25 g,99.8%ee).

Provenance & Evidence