Methanol → HCID 11155476, compound

Participants

Reaction Steps

In 60 ml of a (1:1) mixed solvent of methanol and acetonitrile, 0.50 g (1.3 mmol) of (E)-1-(α-cylopropylcarbonyl-2-fluorobenzyl)-3-carboxymethylidene-4-mercaptopiperidine hydrochloride and 0.05 ml of dimethyl disulfide were dissolved, followed by exposure to light for 90 minutes under cooling by using a low-pressure mercury lamp of 32 W. After the completion of the reaction, the reaction mixture was concentrated by evaporation under reduced pressure. The residue was subjected to high-performance liquid chromatography (column: TSK-GEL ODS-80TS, mobile phase; acetonitrile/water=3/7 (containing 0.016% of trifluoroacetic acid), temperature: room temperature), whereby two diastereomers of the title compound, that is, 14.0 mg (Isomer A) and 13.5 mg (Isomer B) were obtained, each as white powder (amorphous). The retention times of Isomer A and Isomer B in high-performance liquid chromatography (column: Inertsil ODS-2, mobile phase: acetonitrile/water=20/80 (containing 0.02% of trifluoroacetic acid), temperature: 27° C., flow rate: 1.5 ml/min) were 16.5 minutes and 18.5 minutes, respectively.

Provenance & Evidence