Methanesulfonic Acid → HCID 10563488, compound

Participants

Reaction Conditions

Reaction Steps

This compound was isomerized to the fumaryl monoamide using the following procedure. (Z)-N-(3-Carboxy-1-oxo-2-propenyl) -L-phenylalanine (260.0 g.) was mixed with 2.6 1. dry ethyl acetate, 3.80 g. thiourea and 7.19 ml. methanesulfonic acid. The mixture was stirred at reflux temperature for one hour and cooled to 25° C. The crystalline precipitate was collected on a filter, rinsed with 500 ml. ethyl acetate, and dried in air at room temperature to constant weight. The yield of (E)-N-(3-carboxy-1-oxo-2-propenyl)-L-phenylalanine was 226.5 g. (87.1% of theory). The NMR indicated that no Z-isomer was present.

Provenance & Evidence