Hydrochloric Acid → HCID 131720270, compound

Participants

Reaction Steps

592 mg (3 mmol) of O-benzylserine, 393 mg (3 mmol) of 4-cyano-benzaldehyde and 697 mg (3 mmol) of N-(4-nitro-benzyl)-maleimide in 25 ml of DMF were heated at 110° C. for 5 hours. After cooling the solvent was removed in a vacuum. The crude product was filtered over silica gel with hexane/ethyl acetate and the solvent was removed. Thereafter, the residue was dissolved in a methanol/chloroform (1:5) mixture and dry hydrogen chloride was introduced while cooling with ice. After standing at 4° C. for 14 hours the solution was treated with ether and the colourless precipitate was filtered off and thereafter boiled at reflux for 3 hours with a methanol solution saturated with ammonia. The solvent was removed in a vacuum. The thus-obtained crude product was treated with 3 ml of 1N hydrochloric acid and again evaporated. The yellowish residue was separated over a RP-18 chromatography column with a water/methanol gradient. 67 mg of (1RS,3RS,3aSR,6aRS)-4-[3-(benzyloxy-methyl)-5-(4-nitro-benzyl)-4,6-dioxo-octahydro-pyrrolo[3,4-c]pyrrol-1-yl]-benzimidamide hydrochloride were isolated as a yellowish powder. ISP-MS: 514 ([M+H]+, 100).

Provenance & Evidence