Hydrochloric Acid → HCID 14124495, compound

Participants

Reaction Steps

(2R,4S)-1-(p-Nitrobenzyloxycarbonyl)-2-carboxymethyl-4-acetylthiopyrrolidine (153 mg) was dissolved in 2 ml of dry tetrahydrofuran, and 61 mg of triethylamine was added thereto. Ethyl chloroformate (65 mg) was added thereto at -10° to -15° C. under nitrogen stream, followed by stirring at the same temperature for 30 minutes. A 30% ethanol solution of methylamine (414 mg) was added thereto at -40° C., and stirring was continued at -20° to -30° C. for 1 hour. The reaction mixture was acidified with dilute hydrochloric acid, diluted with ethyl acetate, washed successively with water, a saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate and distilled to remove the solvent. The residue was purified by silica gel thin layer chromatography to obtain (2R,4S)-1-(p-nitrobenzyloxycarbonyl)-2-methylaminocarbonylmethyl-4-mercaptopyrrolidine.

Provenance & Evidence